2′-Fluoro-3′,5′-dimethoxy­acetanilide

Xie, K.; Lou, Y.; Zheng, J.; Zhao, Q.; Wei, Y.

doi:10.1107/S1600536808042554

Volume 65
Part 1
Page o205
January 2009

Received 24 November 2008
Accepted 14 December 2008
Online 24 December 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.121
Data-to-parameter ratio = 12.8
Details

2'-Fluoro-3',5'-dimethoxyacetanilide

Kai Xie,^a Yuan-yuan Lou,^a Jin Zheng,^b Qing-jie Zhao ^b and Ya-bing Wei ^a ^*

^aCollege of Materials Science and Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bShanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People's Republic of China
Correspondence e-mail: ybwei@njut.edu.cn

Molecules of the title compound, C₁₀H₁₂FNO₃, are nearly planar considering all non-H atoms with a mean deviation of 0.0288 Å. Molecules are linked through intermolecular N-HO and N-HF hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987). For the synthesis, see: Borodkin et al. (2006); Stavber et al. (2002).

Experimental

Crystal data

C₁₀H₁₂FNO₃
M_r = 213.21
Monoclinic, P 2₁ /c
a = 9.741 (3) Å
b = 4.8439 (12) Å
c = 21.634 (6) Å
= 98.082 (3)°
V = 1010.7 (4) Å³
Z = 4
Mo K radiation
= 0.12 mm^-1
T = 296 (2) K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.977, T_max = 0.989
4791 measured reflections
1780 independent reflections
1434 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.121
S = 1.02
1780 reflections
139 parameters
H-atom parameters constrained
_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
N1-H1O1ⁱ	0.86	2.61	3.246 (2)	131
N1-H1F1ⁱ	0.86	2.47	3.3128 (19)	166
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2815 ).

Acknowledgements

Acknowledgement is made to the crew of Topharman Shanghai Co Ltd for their active cooperation in this work. We also thank Instrument Analysis and Research Center of Shanghai University for structural confirmation.

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.
Borodkin, G. I., Zaikin, P. A. & Shubin, V. G. (2006). Tetrahedron Lett. 47, 15, 2639-2642.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stavber, S., Jereb, M. & Zupan, M. (2002). J. Phys. Org. Chem. 15, 1, 56-61.

organic compounds