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Volume 69 
Part 12 
Page o1749  
December 2013  

Received 12 October 2013
Accepted 31 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.010 Å
Disorder in main residue
R = 0.044
wR = 0.105
Data-to-parameter ratio = 11.5
Details
Open access

2,2,2-Tri­fluoro-N-(2-iodo­phen­yl)acetamide

aJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, People's Republic of China
Correspondence e-mail: ouyangruchun@aliyun.com

The three F atoms in the title compound, C8H5F3INO, are disordered over two sets of sites [relative occupancies = 0.615 (14):0.385 (14)]. In the crystal, mol­ecules are linked by N-H...O hydrogen bonds, forming chains running along the c-axis direction. The dihedral angle between the ring and the amide group is 62.1 (3)°.

Related literature

For effects of flourine on the properties of compounds, see: Jeschke (2004[Jeschke, P. (2004). Chembiochem, 5, 570-589.]); Mueller et al. (2007[Mueller, K., Faeh, C. & Diederich, F. (2007). Science, 317, 1881-1886.]); Purser et al. (2008[Purser, S., Moore, P. R., Swallow, S. & Gouverneur, V. (2008). Chem. Soc. Rev. 37, 320-330.]). For the synthesis, see: Konfink et al. (2007[Konfink, C. C., Blank, B., Pagano, B., Gotz, N. & Knochel, P. (2007). Chem. Commun. 19, 1954-1956.]).

[Scheme 1]

Experimental

Crystal data
  • C8H5F3INO

  • Mr = 315.02

  • Tetragonal, I 41 /a

  • a = 15.8871 (1) Å

  • c = 15.9300 (2) Å

  • V = 4020.7 (6) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 3.20 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.447, Tmax = 0.567

  • 6063 measured reflections

  • 1775 independent reflections

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

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.105

  • S = 1.06

  • 1775 reflections

  • 155 parameters

  • 450 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.08 2.917 (6) 163
Symmetry code: (i) [y+{\script{1\over 4}}, -x+{\script{5\over 4}}, z+{\script{1\over 4}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2122 ).


Acknowledgements

This work was supported by the Science Fund of the Education Office of Jiangxi (GJJ12583) and the Bureau of Science and Technology of Nanchang City.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Jeschke, P. (2004). Chembiochem, 5, 570-589.  [CrossRef] [ChemPort]
Konfink, C. C., Blank, B., Pagano, B., Gotz, N. & Knochel, P. (2007). Chem. Commun. 19, 1954-1956.
Mueller, K., Faeh, C. & Diederich, F. (2007). Science, 317, 1881-1886.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Purser, S., Moore, P. R., Swallow, S. & Gouverneur, V. (2008). Chem. Soc. Rev. 37, 320-330.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1749  [ doi:10.1107/S1600536813029851 ]

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