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Volume 68 
Part 1 
Page o175  
January 2012  

Received 16 November 2011
Accepted 4 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.062
wR = 0.191
Data-to-parameter ratio = 12.1
Details
Open access

4-[(E)-(4-Fluorobenzylidene)amino]benzoic acid

aFacultad de Ciencias Químicas, Universidad Autónoma de Nuevo León, San Nicolás de los Garza, 66451 Nuevo León, Mexico,bDepartamento de Química, Centro de Investigación y de Estudios Avanzados, del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México, DF, Mexico, and cDepartamento de Química Analítica Facultad de Medicina, Universidad Autónoma de Nuevo León, León PO Box 2316, 64841 Nuevo León, Mexico
Correspondence e-mail: blanca.munozfl@uanl.edu.mx

In the title compound, C14H10FNO2, the benzene rings make a dihedral angle of 57.50 (13)°, and the molecule has an E configuration about the C=N bond. In the crystal, molecules are linked via pairs of O-H...O hydrogen bonds, forming inversion dimers.

Related literature

For the synthesis, properties and uses of 4-(benzylideneamino)benzoic acid, see: Borisova et al. (2007[Borisova, N. E., Reshetova, M. D. & Ustynyuk, Y. A. (2007). Chem. Rev. 107, 46-79.]); Schiff (1864[Schiff, H. (1864). Annalen, 131, 118-119.]); Innocenzi & Lebeau (2005[Innocenzi, P. & Lebeau, B. (2005). J. Mater. Chem. 15, 3821-3831.]); Muñoz-Flores et al. (2008[Muñoz-Flores, B. M., Santillan, R., Rodríguez, M., Méndez, J. M., Romero, M., Farfán, N., Lacroix, P. G., Nakatani, K., Ramos-Ortíz, G. & Maldonado, J. L. (2008). J. Organomet. Chem. 693, 1321-1334.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10FNO2

  • Mr = 243.24

  • Monoclinic, P 21 /n

  • a = 12.2787 (5) Å

  • b = 5.6264 (2) Å

  • c = 17.2874 (8) Å

  • [beta] = 105.833 (2)°

  • V = 1148.99 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.23 × 0.2 × 0.15 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 9975 measured reflections

  • 2002 independent reflections

  • 1226 reflections with I > 2[sigma](I)

  • Rint = 0.186

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.191

  • S = 1.04

  • 2002 reflections

  • 166 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H...O1i 0.85 (1) 1.79 (2) 2.601 (3) 159 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: XSCANS (Bruker, 2000[Bruker (2000). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: XSCANS; 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2486 ).


Acknowledgements

The authors thank the Programa de Mejoramiento del Profesorado (PROMEP; grant No. 103.5/11/4330) and the Consejo Nacional de Ciencia y Tecnología (CONACYT; grant No. 82605) for financial support.

References

Borisova, N. E., Reshetova, M. D. & Ustynyuk, Y. A. (2007). Chem. Rev. 107, 46-79.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2000). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.
Innocenzi, P. & Lebeau, B. (2005). J. Mater. Chem. 15, 3821-3831.  [CrossRef] [ChemPort]
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]
Muñoz-Flores, B. M., Santillan, R., Rodríguez, M., Méndez, J. M., Romero, M., Farfán, N., Lacroix, P. G., Nakatani, K., Ramos-Ortíz, G. & Maldonado, J. L. (2008). J. Organomet. Chem. 693, 1321-1334.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Schiff, H. (1864). Annalen, 131, 118-119.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o175  [ doi:10.1107/S1600536811052275 ]

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