N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexa­fluoro­prop­oxy)phen­yl]amino­carbon­yl}-2,6-difluoro­benzamide

Liu, Y.; Li, F.; Li, Y.

doi:10.1107/S1600536808025506

Volume 64
Part 9
Page o1756
September 2008

Received 6 August 2008
Accepted 8 August 2008
Online 13 August 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.009 Å
R = 0.086
wR = 0.248
Data-to-parameter ratio = 12.8
Details

N-{[2,5-Dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]aminocarbonyl}-2,6-difluorobenzamide

Yin-hong Liu,^a Fang-shi Li ^a ^* and Yi Li ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China
Correspondence e-mail: fangshi.li@njut.edu.cn

In the molecule of the title compound, C₁₇H₈Cl₂F₈N₂O₃, the two aromatic rings are oriented at a dihedral angle of 50.12 (3)°. Intramolecular N-HO, C-HO and N-HCl hydrogen bonds result in the formation of two six- and one five-membered rings. The six-membered rings have flattened-boat conformations, while the five-membered ring adopts an envelope conformation. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For related literature, see: Drabek & Boeger (1986). For bond-length data, see: Allen et al. (1987). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₈Cl₂F₈N₂O₃
M_r = 511.15
Monoclinic, P 2₁ /n
a = 9.2300 (18) Å
b = 16.404 (3) Å
c = 14.074 (3) Å
= 108.77 (3)°
V = 2017.6 (8) Å³
Z = 4
Mo K radiation
= 0.42 mm^-1
T = 294 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.851, T_max = 0.921
3609 measured reflections
3609 independent reflections
1922 reflections with I > 2(I)
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2(F²)] = 0.086
wR(F²) = 0.247
S = 1.09
3609 reflections
283 parameters
96 restraints
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2ACl2	0.86	2.43	2.892 (4)	115
N2-H2AO1	0.86	1.98	2.664 (6)	135
N1-H1AO2ⁱ	0.86	1.98	2.814 (6)	163
C10-H10AO2	0.93	2.28	2.851 (6)	119
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2510 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Drabek, J. & Boeger, M. (1986). European Patent No. 179022.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds