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Volume 65 
Part 3 
Page o556  
March 2009  

Received 12 February 2009
Accepted 13 February 2009
Online 21 February 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.139
Data-to-parameter ratio = 21.1
Details
Open access

Ethyl 4-fluoro-3-nitrobenzoate

aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C9H8FNO4, C-H...O intermolecular interactions form dimers with R22(10) motifs. These dimers are arranged into chains parallel to the b axis and the chains are stacked down the c axis.

Related literature

For general background, see: Ishida et al. (2006[Ishida, T., Suzuki, T., Hirashima, S., Mizutani, K., Yoshida, A., Ando, I., Ikeda, S., Adachi, T. & Hashimoto, H. (2006). Bioorg. Med. Chem. Lett. 16, 1859-1863.]); Rida et al. (2005[Rida, S. M., Ashour, F. A., El-Hawash, S. A. M., ElSemary, M. M., Badr, M. H. & Shalaby, M. A. (2005). Eur. J. Med. Chem. 40, 949-959.]); Mohd. Maidin, Abdul Rahim, Abdul Hamid et al. (2008[Mohd. Maidin, S. M., Abdul Rahim, A. S., Abdul Hamid, S., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1501-o1502.]). For bond-length data, see: Allen et al. (1987[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.]). For related structures, see: Mohd. Maidin, Abdul Rahim, Osman et al. (2008[Mohd. Maidin, S. M., Abdul Rahim, A. S., Osman, H., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1550-o1551.]); Li et al. (2008[Li, H.-Y., Liu, B.-N., Tang, S.-G., Xu, Y.-M. & Guo, C. (2008). Acta Cryst. E64, o523.], 2009[Li, H.-Y., Liu, B.-N., Tang, S.-G. & Guo, C. (2009). Acta Cryst. E65, o91.]). For details of hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For details on the stability of the temperature controller, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8FNO4

  • Mr = 213.16

  • Monoclinic, P 21 /c

  • a = 9.9246 (3) Å

  • b = 13.2883 (3) Å

  • c = 6.9310 (2) Å

  • [beta] = 94.410 (2)°

  • V = 911.36 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 100 K

  • 0.55 × 0.22 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.929, Tmax = 0.988

  • 12540 measured reflections

  • 2913 independent reflections

  • 2411 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.139

  • S = 1.11

  • 2913 reflections

  • 138 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1A...O4i 0.93 2.44 3.2380 (15) 144
Symmetry code: (i) -x-1, -y, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2723 ).


Acknowledgements

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. Funding from the Malaysian Government and Universiti Sains Malaysia (USM) under USM Research University grant (1001/PFARMASI/815026) is gratefully acknowledged. SNNB thanks Universiti Sains Malaysia for a Postdoctoral Research Fellowship.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Ishida, T., Suzuki, T., Hirashima, S., Mizutani, K., Yoshida, A., Ando, I., Ikeda, S., Adachi, T. & Hashimoto, H. (2006). Bioorg. Med. Chem. Lett. 16, 1859-1863.  [CrossRef] [PubMed] [ChemPort]
Li, H.-Y., Liu, B.-N., Tang, S.-G. & Guo, C. (2009). Acta Cryst. E65, o91.  [CSD] [CrossRef] [details]
Li, H.-Y., Liu, B.-N., Tang, S.-G., Xu, Y.-M. & Guo, C. (2008). Acta Cryst. E64, o523.  [CSD] [CrossRef] [details]
Mohd. Maidin, S. M., Abdul Rahim, A. S., Abdul Hamid, S., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1501-o1502.  [CSD] [CrossRef] [details]
Mohd. Maidin, S. M., Abdul Rahim, A. S., Osman, H., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1550-o1551.  [CSD] [CrossRef] [details]
Rida, S. M., Ashour, F. A., El-Hawash, S. A. M., ElSemary, M. M., Badr, M. H. & Shalaby, M. A. (2005). Eur. J. Med. Chem. 40, 949-959.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2009). E65, o556  [ doi:10.1107/S1600536809005224 ]

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