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Volume 69 
Part 6 
Page o961  
June 2013  

Received 16 April 2013
Accepted 17 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.094
Data-to-parameter ratio = 19.3
Details
Open access

2-[(3,4-Dichlorobenzylidene)amino]-4-methylphenol

aChemistry Department, K. Maras Sutcuimam University, 46100 K. Maras, Turkey,bChemistry Department, Cukurova University, 01330, Turkey, and cChemistry Department, Loughborough University, Leicestershire LE11 3TU, England
Correspondence e-mail: muhammetkose@ksu.edu.tr

In the title compound, C14H11Cl2NO, the dihedral angle between the benzene rings is 15.36 (8)°. A phenol-imine-type intramolecular O-H...N hydrogen bond generates an S(5) ring motif. In the crystal, a pair of weak C-H...O hydrogen bonds form an R21(7) ring motif involving glide-plane-related molecules. The molecules linked via these interactions form chains along [101].

Related literature

For Schiff bases, see: Akine & Nabeshima (2009[Akine, S. & Nabeshima, T. (2009). Dalton Trans. pp. 10395-10408.]); Vigato & Tamburini (2004[Vigato, P. A. & Tamburini, S. (2004). Coord. Chem. Rev. 248, 1717-2128.]). For related structures, see: Efil et al. (2012[Efil, K., Sen, F., Bekdemir, Y. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1696.]); Fridman & Kaftory (2007[Fridman, N. & Kaftory, M. (2007). Pol. J. Chem. 81, 825-832.]); Jiao et al. (2006[Jiao, Y.-H., Zhang, Q. & Ng, S. W. (2006). Acta Cryst. E62, o3614-o3615.]); Wang & Wang (2007[Wang, Q. & Wang, D.-Q. (2007). Acta Cryst. E63, o4838.]). For hydrogen-bond motifs, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11Cl2NO

  • Mr = 280.14

  • Monoclinic, P 21 /n

  • a = 4.6074 (7) Å

  • b = 21.680 (3) Å

  • c = 12.7907 (18) Å

  • [beta] = 93.342 (2)°

  • V = 1275.5 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.49 mm-1

  • T = 150 K

  • 0.64 × 0.14 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2009[Sheldrick, G. M. (2009). SADABS. University of Göttingen, Germany.]) Tmin = 0.743, Tmax = 0.966

  • 12828 measured reflections

  • 3159 independent reflections

  • 2556 reflections with I2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.094

  • S = 1.02

  • 3159 reflections

  • 164 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O1i 0.95 2.67 3.618 (2) 174
C8-H8...O1i 0.95 2.65 3.562 (2) 162
O1-H1...N1 0.81 2.16 2.6612 (17) 121
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 1998[Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2096 ).


Acknowledgements

We are grateful to Loughborough University for the data collection and Cukurova University for financial support (to IG).

References

Akine, S. & Nabeshima, T. (2009). Dalton Trans. pp. 10395-10408.  [CrossRef]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Efil, K., Sen, F., Bekdemir, Y. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1696.  [CSD] [CrossRef] [details]
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fridman, N. & Kaftory, M. (2007). Pol. J. Chem. 81, 825-832.  [ChemPort]
Jiao, Y.-H., Zhang, Q. & Ng, S. W. (2006). Acta Cryst. E62, o3614-o3615.  [CSD] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2009). SADABS. University of Göttingen, Germany.
Vigato, P. A. & Tamburini, S. (2004). Coord. Chem. Rev. 248, 1717-2128.  [ISI] [CrossRef] [ChemPort]
Wang, Q. & Wang, D.-Q. (2007). Acta Cryst. E63, o4838.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o961  [ doi:10.1107/S1600536813013585 ]

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