N-(4-chloro­benzo­yl)-N-(2-chloro­phen­yl)-O-[2-(2-nitro­phen­yl)acet­yl]hydroxyl­amine

Ma, J.; Ma, Y.; He, D.

doi:10.1107/S1600536812040883

Volume 68
Part 11
Page o3067
November 2012

Received 20 September 2012
Accepted 28 September 2012
Online 3 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.008 Å
R = 0.054
wR = 0.069
Data-to-parameter ratio = 13.5
Details

N-(4-chlorobenzoyl)-N-(2-chlorophenyl)-O-[2-(2-nitrophenyl)acetyl]hydroxylamine

Jing Ma,^a ^* Yi Ma ^b and Dian He ^a

^aInstitute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China, and ^bGansu College of Traditional Chinese Medicine, Lanzhou 730000, Gansu Province, People's Republic of China
Correspondence e-mail: majing.1988.ok@163.com

In the title hydroxamic acid derivate, C₂₁H₁₄N₂O₅Cl₂, the nitro-substituted benzene ring forms dihedral angles of 66.0 (2) and 59.6 (2)°, with the p-chloro and o-chloro-substituted benzene rings, respectively. The dihedral angle between the two chloro-substituted benzene rings is 64.2 (2) Å. In the crystal, weak C-HO hydrogen bonds link the molecules along [010]. The crystal studied was an inversion twin with refined components in the ratio 0.60 (7):0.40 (7).

Related literature

For applications of hydroxamic acid derivatives, see: Noh et al. (2009); Zeng et al. (2003). For the synthesis, see: Ayyangark et al. (1986). For a related structure, see: Zhang et al. (2012).

Experimental

Crystal data

C₂₁H₁₄Cl₂N₂O₅
M_r = 445.24
Monoclinic, P 2₁
a = 12.366 (14) Å
b = 6.789 (8) Å
c = 12.579 (14) Å
= 105.150 (14)°
V = 1019 (2) Å³
Z = 2
Mo K radiation
= 0.36 mm^-1
T = 296 K
0.21 × 0.20 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.929, T_max = 0.945
5091 measured reflections
3669 independent reflections
1821 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.069
S = 0.99
3669 reflections
271 parameters
1 restraint
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 1624 Friedel pairs
Flack parameter: 0.40 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O1ⁱ	0.93	2.38	3.264 (7)	158
C15-H15BO1ⁱⁱ	0.97	2.45	3.421 (6)	175
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5536 ).

Acknowledgements

This work was supported by the Natural Science Fund Projects of Gansu Province (0710RJZA124).

References

Ayyangark, N. R., Hrailme, C., Kalkotf, U. R. & Srinivasan, K. V. (1986). Synth. Commun. pp. 938-941.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Noh, E. J., Lim, D. S., Jeong, G. & Lee, J. S. (2009). Biochem. Biophys. Res. Commun. 378, 326-331.
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zeng, W., Zeng, G. Y. & Qin, S. Y. (2003). Chin. J. Org. Chem. 23, 1213-1218.
Zhang, H., Qu, D. & Ma, J. (2012). Acta Cryst. E68, o2904.

organic compounds