Ethyl 4-fluoro-3-nitro­benzoate

Narendra Babu, S.N.; Abdul Rahim, A.S.; Osman, H.; Razak, I.A.; Fun, H.-K.

doi:10.1107/S1600536809005224

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.139
Data-to-parameter ratio = 21.1
Details

Ethyl 4-fluoro-3-nitrobenzoate

Shivanagere Nagojappa Narendra Babu,^a Aisyah Saad Abdul Rahim,^a ⁺ Hasnah Osman,^b Ibrahim Abdul Razak ^c and Hoong-Kun Fun ^c ^*

^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-HO 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); Rida et al. (2005); Mohd. Maidin, Abdul Rahim, Abdul Hamid et al. (2008). For bond-length data, see: Allen et al. (1987). For related structures, see: Mohd. Maidin, Abdul Rahim, Osman et al. (2008); Li et al. (2008, 2009). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For details on the stability of the temperature controller, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₉H₈FNO₄
M_r = 213.16
Monoclinic, P 2₁ /c
a = 9.9246 (3) Å
b = 13.2883 (3) Å
c = 6.9310 (2) Å
= 94.410 (2)°
V = 911.36 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.929, T_max = 0.988
12540 measured reflections
2913 independent reflections
2411 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.139
S = 1.11
2913 reflections
138 parameters
H-atom parameters constrained
_max = 0.55 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1AO4ⁱ	0.93	2.44	3.2380 (15)	144
Symmetry code: (i) -x-1, -y, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
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.
Li, H.-Y., Liu, B.-N., Tang, S.-G. & Guo, C. (2009). Acta Cryst. E65, o91.
Li, H.-Y., Liu, B.-N., Tang, S.-G., Xu, Y.-M. & Guo, C. (2008). Acta Cryst. E64, o523.
Mohd. Maidin, S. M., Abdul Rahim, A. S., Abdul Hamid, S., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1501-o1502.
Mohd. Maidin, S. M., Abdul Rahim, A. S., Osman, H., Kia, R. & Fun, H.-K. (2008). Acta Cryst. E64, o1550-o1551.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds