5-Chloro-2-nitro­phenol

Ren, D.

doi:10.1107/S1600536812014638

Volume 68
Part 5
Page o1365
May 2012

Received 1 April 2012
Accepted 4 April 2012
Online 13 April 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.171
Data-to-parameter ratio = 13.0
Details

5-Chloro-2-nitrophenol

Dong-mei Ren ^a ^*

^aSecurity and Environment Engineering College, Capital University of Economics and Business, Beijing 10070, People's Republic of China
Correspondence e-mail: nanoren@126.com

The asymmetric unit of the title compound, C₆H₄ClNO₃, contains two independent molecules in which the dihedral angles between the benzene ring and the nitro groups are 2.5 (1) and 8.5 (1)°. Intramolecular O-HO hydrogen bonds involving the hydroxy and nitro substituents result in the formation of S(6) six-membered rings. In the crystal, O-HO, O-HCl and C-HO hydrogen bonds together with ClO contacts [3.238 (3) and 3.207 (3) Å] generate a three-dimensional network.

Related literature

For background to applications of the title compound and its synthesis, see: Richard (1971). For bond-length data, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₆H₄ClNO₃
M_r = 173.55
Triclinic, $[P \overline 1]$
a = 7.5390 (15) Å
b = 8.1640 (16) Å
c = 13.132 (3) Å
= 94.75 (3)°
= 96.48 (3)°
= 116.46 (3)°
V = 710.9 (2) Å³
Z = 4
Mo K radiation
= 0.49 mm^-1
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.909, T_max = 0.953
2808 measured reflections
2596 independent reflections
1833 reflections with I > 2(I)
R_int = 0.075
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.171
S = 1.01
2596 reflections
200 parameters
H-atom parameters constrained
_max = 0.32 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3AO2	0.82	1.91	2.605 (5)	142
O6-H6AO4	0.82	1.88	2.581 (4)	143
O3-H3AO6ⁱ	0.82	2.71	3.350 (5)	136
O6-H6ACl2ⁱⁱ	0.82	2.70	3.207 (3)	121
C2-H2AO5ⁱⁱⁱ	0.93	2.49	3.155 (5)	129
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x, y-1, z; (iii) -x+1, -y, -z+1.

Data collection: CAD-4 Software (Enraf-Nonius, 1985); 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: 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: SJ5233 ).

Acknowledgements

This study was supported financially by the Capital University of Economics and Business (00891162721716) and the Scientific Research Level Project of the Beijing Education Commission Foundation. The author thanks the Center of Testing and Analysis, Beijing University of Science and Technology, for the data collection.

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.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
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.
Richard, L. J. (1971). J. Org. Chem. 36, 242-243.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds