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Volume 69 
Part 8 
Page o1349  
August 2013  

Received 10 July 2013
Accepted 14 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.100
Data-to-parameter ratio = 14.1
Details
Open access

2-[(E)-(5-Chloro-2-methylphenyl)iminomethyl]-4-methylphenol

aDepartment of Chemistry, Lishui University, Lishui 323000, People's Republic of China
Correspondence e-mail: fan200203@163.com

In the molecule of the title Schiff base compound, C15H14ClNO, the two benzene rings are twisted with respect to each other, with a dihedral angle of 35.0 (3)°; an intramolecular O-H...N hydrogen bond occurs. In the crystal, weak C-H...[pi] interactions between methyl groups and chlorophenyl rings link the molecules into supramolecular chains running along the a axis.

Related literature

For background to phyenylamine compounds, see: Fan et al. (2012[Fan, C.-B., Wang, X.-M., Ding, P., Wang, J.-J., Liang, Z.-Q. & Tao, X.-T. (2012). Dyes Pigm. 95, 757-767.]). For applications of Schiff base derivatives, see: Siddiqui et al. (2006[Siddiqui, J. I., Iqbal, A., Ahmad, S. & Weaver, G. W. (2006). Molecules, 11, 206-211.]); Ebrahimipour et al. (2012[Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14ClNO

  • Mr = 259.72

  • Orthorhombic, P 21 21 21

  • a = 7.6629 (10) Å

  • b = 11.8442 (14) Å

  • c = 14.342 (2) Å

  • V = 1301.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.45 × 0.42 × 0.35 mm

Data collection
  • Agilent Xcalibur Gemini ultra diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.88, Tmax = 0.91

  • 8663 measured reflections

  • 2382 independent reflections

  • 1769 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.100

  • S = 1.03

  • 2382 reflections

  • 169 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 991 Friedel pairs

  • Absolute structure parameter: -0.18 (9)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9-C14 benzene ring.

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.84 (4) 1.84 (4) 2.629 (3) 154 (4)
C7-H7C...Cg1i 0.96 2.91 3.767 (3) 149
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5720 ).


Acknowledgements

The author acknowledges Lishui University for financial support.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Ebrahimipour, S. Y., Mague, J. T., Akbari, A. & Takjoo, R. (2012). J. Mol. Struct. 1028, 148-155.
Fan, C.-B., Wang, X.-M., Ding, P., Wang, J.-J., Liang, Z.-Q. & Tao, X.-T. (2012). Dyes Pigm. 95, 757-767.  [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
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 (2013). E69, o1349  [ doi:10.1107/S1600536813019454 ]

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