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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 [sigma](C-C) = 0.008 Å
R = 0.054
wR = 0.069
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...O 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[Noh, E. J., Lim, D. S., Jeong, G. & Lee, J. S. (2009). Biochem. Biophys. Res. Commun. 378, 326-331.]); Zeng et al. (2003[Zeng, W., Zeng, G. Y. & Qin, S. Y. (2003). Chin. J. Org. Chem. 23, 1213-1218.]). For the synthesis, see: Ayyangark et al. (1986[Ayyangark, N. R., Hrailme, C., Kalkotf, U. R. & Srinivasan, K. V. (1986). Synth. Commun. pp. 938-941.]). For a related structure, see: Zhang et al. (2012[Zhang, H., Qu, D. & Ma, J. (2012). Acta Cryst. E68, o2904.]).

[Scheme 1]

Experimental

Crystal data
  • C21H14Cl2N2O5

  • Mr = 445.24

  • Monoclinic, P 21

  • a = 12.366 (14) Å

  • b = 6.789 (8) Å

  • c = 12.579 (14) Å

  • [beta] = 105.150 (14)°

  • V = 1019 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.]) Tmin = 0.929, Tmax = 0.945

  • 5091 measured reflections

  • 3669 independent reflections

  • 1821 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.069

  • S = 0.99

  • 3669 reflections

  • 271 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1624 Friedel pairs

  • Flack parameter: 0.40 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O1i 0.93 2.38 3.264 (7) 158
C15-H15B...O1ii 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[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CrossRef] [details]
Noh, E. J., Lim, D. S., Jeong, G. & Lee, J. S. (2009). Biochem. Biophys. Res. Commun. 378, 326-331.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zeng, W., Zeng, G. Y. & Qin, S. Y. (2003). Chin. J. Org. Chem. 23, 1213-1218.  [ChemPort]
Zhang, H., Qu, D. & Ma, J. (2012). Acta Cryst. E68, o2904.  [CrossRef] [details]


Acta Cryst (2012). E68, o3067  [ doi:10.1107/S1600536812040883 ]

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