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

Muñoz-Flores, B.M.; Pérez, V.M.J.; Santillan, R.L.; Ochoa, M.E.; Waksman, N.

doi:10.1107/S1600536811052275

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 (C-C) = 0.004 Å
R = 0.062
wR = 0.191
Data-to-parameter ratio = 12.1
Details

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

Blanca M. Muñoz-Flores,^a ^* Víctor M. Jiménez Pérez,^a Rosa L. Santillan,^b Maria Eugenia Ochoa ^b and Noemi Waksman ^c

^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-HO hydrogen bonds, forming inversion dimers.

Related literature

For the synthesis, properties and uses of 4-(benzylideneamino)benzoic acid, see: Borisova et al. (2007); Schiff (1864); Innocenzi & Lebeau (2005); Muñoz-Flores et al. (2008).

Experimental

Crystal data

C₁₄H₁₀FNO₂
M_r = 243.24
Monoclinic, P 2₁ /n
a = 12.2787 (5) Å
b = 5.6264 (2) Å
c = 17.2874 (8) Å
= 105.833 (2)°
V = 1148.99 (8) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.186

Refinement

R[F² > 2(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
_max = 0.18 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-HO1ⁱ	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); cell refinement: XSCANS (Bruker, 2000); data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); 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.
Bruker (2000). XSCANS. Bruker AXS Inc., Madison, Wisconsin, USA.
Innocenzi, P. & Lebeau, B. (2005). J. Mater. Chem. 15, 3821-3831.
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.
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.

organic compounds