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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 [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.100
Data-to-parameter ratio = 11.2
Details
Open access

2-Amino-5-fluorobenzoic acid

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-H...O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by pairs of O-H...O hydrogen bonds generate R22(8) loops. Weak N-H...F hydrogen bonds, short F...F 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[Toyn, J. H., Gunyuzlu, P. L., White, W. H., Thompson, L. A. & Hollis, G. F. (2000). Yeast. 16, 553-560.]).

[Scheme 1]

Experimental

Crystal data
  • C7H6FNO2

  • Mr = 155.13

  • Monoclinic, P 21 /c

  • a = 4.9346 (2) Å

  • b = 11.7542 (6) Å

  • c = 11.9727 (5) Å

  • [beta] = 96.782 (3)°

  • V = 689.58 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.947, Tmax = 0.969

  • 5184 measured reflections

  • 1207 independent reflections

  • 1057 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.11 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1B...O1 0.901 (19) 2.044 (19) 2.6959 (17) 128.2 (16)
N1-H1A...F1i 0.91 (2) 2.55 (2) 3.3646 (17) 149.8 (14)
O2-H2...O1ii 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[Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]);; cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Toyn, J. H., Gunyuzlu, P. L., White, W. H., Thompson, L. A. & Hollis, G. F. (2000). Yeast. 16, 553-560.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o387  [ doi:10.1107/S160053681300408X ]

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