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Volume 70 
Part 1 
Page o42  
January 2014  

Received 4 December 2013
Accepted 9 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.056
wR = 0.153
Data-to-parameter ratio = 13.0
Details
Open access

4-Chloro-2-[(E)-(4-fluoro­phen­yl)imino­meth­yl]phenol

aCollege of Mathematics and Physics, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: fengtj707@126.com

In the title Schiff base mol­ecule, C13H9ClFNO, the benzene rings are twisted slightly with respect to each other, making a dihedral angle of 7.92 (2)°. An intra­molecular O-H...N hydrogen bond occurs. In the crystal, an infinite chain is formed along the c-axis direction by [pi]-[pi] stacking inter­actions between the phenyl rings and the six-membered hydrogen-bonded ring of neighboring Schiff base ligands [centroid-centroid distances of 3.698 (2) and 3.660 (3) Å]. Neighboring chains are linked into a three-dimensional supra­molecular structure by C-H...O and C-H...F hydrogen bonds.

Related literature

For the coordination modes of Schiff base ligands with transition metals, see: Ebrahimipour et al. (2012[Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.]); Guo et al. (2013[Guo, H. F., Zhao, X., Ma, D. Y., Xie, A. P. & Shen, W. B. (2013). Transition Met. Chem. 38, 299-305.]). For the biological activity of Schiff base ligands, see: Sawada et al. (2001[Sawada, H., Yanagida, K., Inaba, Y., Sugiya, M., Kawase, T. & Tomita, T. (2001). Eur. Polym. J. 37, 1433-1439.]); Ma et al. (2013[Ma, D. Y., Zhang, L. X., Rao, X. Y., Wu, T. L., Li, D. H. & Xie, X. Q. (2013). J. Coord. Chem. 66, 1486-1496.]); Siddiqui et al. (2006[Siddiqui, J. I., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206-211.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9ClFNO

  • Mr = 249.66

  • Monoclinic, P 21 /n

  • a = 4.5140 (9) Å

  • b = 20.560 (4) Å

  • c = 12.0712 (19) Å

  • [beta] = 94.153 (16)°

  • V = 1117.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 293 K

  • 0.34 × 0.27 × 0.22 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.908, Tmax = 0.942

  • 6481 measured reflections

  • 2016 independent reflections

  • 1143 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.153

  • S = 1.04

  • 2016 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 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
C7-H7...O1i 0.93 2.69 3.569 (4) 158
C10-H10...F1ii 0.93 2.67 3.481 (4) 147
O1-H1...N1 0.82 1.88 2.613 (3) 148
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+3, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2572 ).


Acknowledgements

The author acknowledges Lanzhou Jiaotong University for supporting this work.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.
Guo, H. F., Zhao, X., Ma, D. Y., Xie, A. P. & Shen, W. B. (2013). Transition Met. Chem. 38, 299-305.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Ma, D. Y., Zhang, L. X., Rao, X. Y., Wu, T. L., Li, D. H. & Xie, X. Q. (2013). J. Coord. Chem. 66, 1486-1496.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sawada, H., Yanagida, K., Inaba, Y., Sugiya, M., Kawase, T. & Tomita, T. (2001). Eur. Polym. J. 37, 1433-1439.  [Web of Science] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddiqui, J. I., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206-211.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2014). E70, o42  [ doi:10.1107/S1600536813033278 ]

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