3,5-Dinitro­benzoyl chloride

Wang, H.-Y.; Xie, M.-H.; Luo, S.-N.; Zou, P.; Liu, Y.-L.

doi:10.1107/S1600536809036228

Volume 65
Part 10
Page o2460
October 2009

Received 27 July 2009
Accepted 8 September 2009
Online 12 September 2009

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.038
wR = 0.097
Data-to-parameter ratio = 12.3
Details

3,5-Dinitrobenzoyl chloride

Hong-Yong Wang,^a Min-Hao Xie,^a ^* Shi-Neng Luo,^a Pei Zou ^a and Ya-Ling Liu ^a

^aJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
Correspondence e-mail: wywhy007@yahoo.com.cn

The carbonyl chloride group in the title compound, C₇H₃ClN₂O₅, is disordered over two orientations with occupancies of 0.505 (5) and 0.495 (5). The molecule is approximately planar, the dihedral angle between the carbonyl chloride plane and benzene ring being 9.6 (4)° in the major disorder component and 7.1 (4)° in the minor component. The nitro group at the 5-position is twisted, forming a dihedral angle of 6.7 (4)°. The crystal packing is stabilized by C-HO hydrogen bonds.

Related literature

For general background to 3,5-dinitrobenzoyl chloride, see: Gennaro et al. (1993); Liu & Wang (2000); Saunders & Stacey (1942).

Experimental

Crystal data

C₇H₃ClN₂O₅
M_r = 230.56
Orthorhombic, P n a 2₁
a = 18.295 (4) Å
b = 8.3924 (19) Å
c = 5.7362 (13) Å
V = 880.7 (3) Å³
Z = 4
Mo K radiation
= 0.44 mm^-1
T = 93 K
0.37 × 0.33 × 0.27 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
6904 measured reflections
2011 independent reflections
1835 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.097
S = 1.03
2011 reflections
164 parameters
29 restraints
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 905 Friedel pairs
Flack parameter: 0.08 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O4ⁱ	0.95	2.44	3.386 (3)	173
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: CI2867 ).

Acknowledgements

The authors acknowledge financial support from the Jiangsu Institute of Nuclear Medicine.

References

Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gennaro, M. C., Abrigo, C., Marengo, E. & Liberatori, A. (1993). J. Liq. Chromatogr. 16, 2715-2730.
Liu, X. J. & Wang, S. Q. (2000). Chin. J. Pharm. 31, 471-472.
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Saunders, B. C. & Stacey, G. L. (1942). J. Biochem. 34, 368-375.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds