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Volume 69 
Part 8 
Page o1234  
August 2013  

Received 5 June 2013
Accepted 27 June 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.128
Data-to-parameter ratio = 17.7
Details
Open access

4-Fluoro-N-[(E)-3,4,5-trimethoxybenzylidene]aniline

aCentre for Crystal Growth, School of Advanced sciences, VIT University, Vellore 632 014, India,bSophisticated Test and Instrumentation Centre (STIC), Cochin University PO, Cochin 682 022, Kerala, India, and cDepartment of Physics, Bangladesh University of Engineering and Technology, Dhaka 1000, Bangladesh
Correspondence e-mail: jpodder@phy.buet.ac.bd

The title compound, C16H16FNO3, exists in a trans configuration with respect to the C=N bond [1.258 (2) Å]. The central methoxy O atom deviates from the plane of the attached benzene ring by 0.0911 (14) Å. The dihedral angle between the aromatic rings is 47.58 (11)°. The crystal structure features C-H...N and C-H...O interactions.

Related literature

For the uses and biological importance of Schiff base compounds, see: Xia et al. (2009[Xia, D.-G., Ye, Y.-F. & Lei, K.-W. (2009). Acta Cryst. E65, o3168.]); Shah et al. (1992[Shah, S., Vyas, R. & Mehta, R. H. (1992). J. Indian Chem. Soc. 69, 590-590.]); Ünver et al. (2004[Ünver, H., Karakas, A. & Elmali, A. (2004). J. Mol. Struct. 702, 49-54.]). For related structures, see: Fun et al. (2011[Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011). Acta Cryst. E67, o1273-o1274.]); Khalaji & Simpson (2009[Khalaji, A. D. & Simpson, J. (2009). Acta Cryst. E65, o553.]); Balachandar et al. (2013[Balachandar, R. K., Kalainathan, S., Eappen, S. M. & Podder, J. (2013). Acta Cryst. E69, o905.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16FNO3

  • Mr = 289.30

  • Monoclinic, P 21

  • a = 7.1147 (9) Å

  • b = 8.3841 (9) Å

  • c = 12.9217 (13) Å

  • [beta] = 105.266 (5)°

  • V = 743.59 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.40 × 0.35 × 0.30 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.971

  • 5699 measured reflections

  • 3358 independent reflections

  • 2468 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.128

  • S = 1.00

  • 3358 reflections

  • 190 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...N1i 0.93 2.57 3.492 (3) 174
C7-H7...O3ii 0.93 2.58 3.504 (3) 173
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x+1, y+{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); 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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2233 ).


Acknowledgements

The authors acknowledge the STIC, Cochin, for the single- crystal XRD facility. They also thank Mr P. Narayanan and Dr K. Sethusankar, RKM Vivekananda College (Autonomous), Chennai 600 004, and VIT University Management for providing the research facilities.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Balachandar, R. K., Kalainathan, S., Eappen, S. M. & Podder, J. (2013). Acta Cryst. E69, o905.  [CrossRef] [IUCr Journals]
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Quah, C. K., Huang, C. & Yu, H. (2011). Acta Cryst. E67, o1273-o1274.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Khalaji, A. D. & Simpson, J. (2009). Acta Cryst. E65, o553.  [CSD] [CrossRef] [IUCr Journals]
Shah, S., Vyas, R. & Mehta, R. H. (1992). J. Indian Chem. Soc. 69, 590-590.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ünver, H., Karakas, A. & Elmali, A. (2004). J. Mol. Struct. 702, 49-54.
Xia, D.-G., Ye, Y.-F. & Lei, K.-W. (2009). Acta Cryst. E65, o3168.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1234  [ doi:10.1107/S1600536813017741 ]

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