N-Benzyl-2,3,4,5,6-penta­fluoro­benz­amide

Valkonen, A.; Lahtinen, T.; Rissanen, K.

doi:10.1107/S1600536810043345

Volume 66
Part 11
Page o3007
November 2010

Received 15 October 2010
Accepted 24 October 2010
Online 31 October 2010

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.086
Data-to-parameter ratio = 11.2
Details

N-Benzyl-2,3,4,5,6-pentafluorobenzamide

Arto Valkonen,^a Tanja Lahtinen ^a and Kari Rissanen ^a ^*

^aNanoscience Center, Department of Chemistry, University of Jyväskylä, PO Box 35, FIN-40014 University of Jyväskylä, Finland
Correspondence e-mail: kari.t.rissanen@jyu.fi

In the title compound, C₁₄H₈F₅NO, the dihedral angle between the planes of the pentafluorophenyl and phenyl rings is 18.34 (5)°. An intermolecular N-HO hydrogen bond between the amide groups connects these molecules to form an infinite chain through the crystal structure. One weak intermolecular C-HO contact and one [pi] - [pi] interaction [centroid-centroid distance = 3.772 (3) Å] are also involved in crystal structure stabilization between the phenyl rings.

Related literature

For related structures, see: An & Rhee (2003); Cockroft et al. (2007); Forbes et al. (2001); Liu et al. (2007); Qadeer et al. (2007); Zhang & Zhang (2008). For anion [pi] interactions, see: Albrecht et al. (2010); Lahtinen & Rissanen (2007); Müller et al. (2010).

Experimental

Crystal data

C₁₄H₈F₅NO
M_r = 301.21
Monoclinic, P 2₁ /n
a = 7.1649 (2) Å
b = 22.9090 (5) Å
c = 7.5363 (1) Å
= 99.205 (2)°
V = 1221.08 (5) Å³
Z = 4
Mo K radiation
= 0.16 mm^-1
T = 123 K
0.40 × 0.28 × 0.26 mm

Data collection

Bruker Nonius KappaCCD with APEXII detector diffractometer
4246 measured reflections
2152 independent reflections
1891 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.086
S = 1.06
2152 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N8-H8O1ⁱ	0.88 (1)	2.01 (1)	2.875 (2)	171 (2)
C5-H5O1ⁱⁱ	0.95	2.37	3.276 (2)	158
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y, z+1.

Data collection: COLLECT (Bruker, 2008); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5380 ).

Acknowledgements

This work was supported by the Academy of Finland (KR, project No. 212588).

References

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organic compounds