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Volume 68 
Part 1 
Page o187  
January 2012  

Received 2 December 2011
Accepted 12 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.054
wR = 0.137
Data-to-parameter ratio = 14.5
Details
Open access

5-Fluoro-1H-indole-3-carboxylic acid

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: seuzzh@sina.com

In the title compound, C9H6FNO2, the carboxyl group is twisted slightly away from the indole-ring plane [dihedral angle = 7.39 (10)°]. In the crystal, carboxyl inversion dimers linked by pairs of O-H...O hydrogen bonds generate R22(8) loops and N-H...O hydrogen bonds connect the dimers into (10[\overline{1}]) sheets.

Related literature

For background to indoles as pharmaceuticals, see: Lang et al. (2011[Lang, L., Wu, J.-L., Shi, L.-J., Xia, C.-G. & Li, F.-W. (2011). Chem. Commun. 47, 12553-12555.]).

[Scheme 1]

Experimental

Crystal data
  • C9H6FNO2

  • Mr = 179.15

  • Monoclinic, P 21 /n

  • a = 4.4176 (9) Å

  • b = 11.073 (2) Å

  • c = 16.014 (3) Å

  • [beta] = 96.63 (3)°

  • V = 778.1 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Rigaku SCXmini CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.982, Tmax = 0.993

  • 7874 measured reflections

  • 1788 independent reflections

  • 1153 reflections with I > 2[sigma](I)

  • Rint = 0.068

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.137

  • S = 1.02

  • 1788 reflections

  • 123 parameters

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 1.86 2.669 (2) 171
N1-H1B...O2ii 0.89 (3) 2.18 (3) 3.026 (2) 159 (2)
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6548 ).


References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Lang, L., Wu, J.-L., Shi, L.-J., Xia, C.-G. & Li, F.-W. (2011). Chem. Commun. 47, 12553-12555.  [CSD] [CrossRef] [ChemPort]
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o187  [ doi:10.1107/S1600536811053426 ]

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