2-Amino-5-fluoro­benzoic acid

Sreenivasa, S.; ManojKumar, K.E.; Suchetan, P.A.; Palakshamurthy, B.S.; Gunasekaran, K.

doi:10.1107/S160053681300408X

Volume 69
Part 3
Page o387
March 2013

Received 10 February 2013
Accepted 11 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.034
wR = 0.100
Data-to-parameter ratio = 11.2
Details

2-Amino-5-fluorobenzoic acid

S. Sreenivasa,^a ^* K.E. ManojKumar,^a P.A. Suchetan,^b B. S. Palakshamurthy ^c and K. Gunasekaran ^d

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,^bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,^cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and ^dCentre of Advanced Study in Crystallography and Biophysics, University of Madras Guindy Campus, Chennai 600 025, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C₇H₆FNO₂, the molecule is almost planar (r.m.s. deviation for the non-H atoms = 0.015 Å) and an intramolecular N-HO hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of O-HO hydrogen bonds generate R₂²(8) loops. Weak N-HF hydrogen bonds, short FF contacts [2.763 (2) Å] and aromatic [pi] - [pi] stacking interactions [centroid-centroid separation = 3.5570 (11) Å] are also observed in the crystal structure.

Related literature

For the applications of the title compound in the field of genetics, see: Toyn et al. (2000).

Experimental

Crystal data

C₇H₆FNO₂
M_r = 155.13
Monoclinic, P 2₁ /c
a = 4.9346 (2) Å
b = 11.7542 (6) Å
c = 11.9727 (5) Å
= 96.782 (3)°
V = 689.58 (5) Å³
Z = 4
Mo K radiation
= 0.13 mm^-1
T = 293 K
0.43 × 0.37 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.947, T_max = 0.969
5184 measured reflections
1207 independent reflections
1057 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.100
S = 1.09
1207 reflections
108 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.11 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BO1	0.901 (19)	2.044 (19)	2.6959 (17)	128.2 (16)
N1-H1AF1ⁱ	0.91 (2)	2.55 (2)	3.3646 (17)	149.8 (14)
O2-H2O1ⁱⁱ	0.82	1.81	2.6279 (12)	175
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2004);; cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7040 ).

Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur, for his constant encouragement. BSPM thanks Dr H. C. Devarajegowda, Department of Physics Yuvarajas College (Constituent), University of Mysore, for his guidance.

References

Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Toyn, J. H., Gunyuzlu, P. L., White, W. H., Thompson, L. A. & Hollis, G. F. (2000). Yeast. 16, 553-560.

organic compounds