[Journal logo]

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 [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.123
Data-to-parameter ratio = 13.2
Details
Open access

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

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-H...N 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[Corke, T. C., Bunce, N. J., Beamount, A. L. & Merrick, R. L. (1979). J. Agric. Food Chem. 27, 644-646.]); Gorrad & Manson (1989[Gorrad, J. W. & Manson, D. (1989). Xenobiotica, 16, 933-955.]). For related structures, see: Jothi et al. (2012[Jothi, L., Vasuki, G., Babu, R. R. & Ramamurthi, K. (2012). Acta Cryst. E68, o772.]); Yaeghoobi et al. (2009[Yaeghoobi, M., Rahman, N. A. & Ng, S. W. (2009). Acta Cryst. E65, o1070.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO

  • Mr = 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[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.123

  • S = 1.07

  • 2042 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.71 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11-C16 ring.

D-H...A D-H H...A D...A D-H...A
O2-H2...N3i 0.84 2.05 2.854 (3) 160
C17-H17C...Cgii 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[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.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort] [ISI]
Gorrad, J. W. & Manson, D. (1989). Xenobiotica, 16, 933-955.
Jothi, L., Vasuki, G., Babu, R. R. & Ramamurthi, K. (2012). Acta Cryst. E68, o772.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yaeghoobi, M., Rahman, N. A. & Ng, S. W. (2009). Acta Cryst. E65, o1070.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3191  [ doi:10.1107/S1600536812043140 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.