1-Chloro­meth­yl-3-nitro­benzene

Abbasi, M.A.; Jahangir, M.; Akkurt, M.; Aziz-ur-Rehman; Khan, I.U.; Sharif, S.

doi:10.1107/S1600536810005076

Volume 66
Part 3
Page o608
March 2010

Received 4 February 2010
Accepted 8 February 2010
Online 13 February 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.116
Data-to-parameter ratio = 19.0
Details

1-Chloromethyl-3-nitrobenzene

Muhammad Athar Abbasi,^a ⁺ Muhammad Jahangir,^a Mehmet Akkurt,^b ^* Aziz-ur-Rehman,^a Islam Ullah Khan ^a and Shahzad Sharif ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title molecule, C₇H₆ClNO₂, the plane of the nitro group and the direction of the chloromethyl group are twisted away from the benzene ring, forming dihedral angles of 8.2 (3) and 67.55 (12)°, respectively. In the crystal structure, weak intermolecular C-HO interactions link the molecules into corrugated sheets parallel to the bc plane.

Related literature

For the characteristics of nitroaromatic compounds, see: Moreno et al. (1986). For details of the synthesis, see: Livermore & Sealock (1947). For reference bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₇H₆ClNO₂
M_r = 171.58
Monoclinic, P 2₁ /c
a = 12.1219 (10) Å
b = 4.5104 (4) Å
c = 15.1219 (11) Å
= 112.709 (2)°
V = 762.69 (11) Å³
Z = 4
Mo K radiation
= 0.44 mm^-1
T = 296 K
0.34 × 0.18 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
8475 measured reflections
1903 independent reflections
1350 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.116
S = 1.03
1903 reflections
100 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O1ⁱ	0.93	2.67	3.583 (3)	166
C6-H6O2ⁱⁱ	0.93	2.67	3.374 (3)	133
Symmetry codes: (i) -x+2, -y+3, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2694 ).

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support.

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.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Livermore, A. H. & Sealock, R. R. (1947). J. Biol. Chem. 167, 699-704.
Moreno, S. N. J., Schreiber, J. & Mason, R. P. (1986). J. Biol. Chem. 261, 7811-7815.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds