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Volume 68 
Part 12 
Page o3498  
December 2012  

Received 14 November 2012
Accepted 27 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.055
wR = 0.139
Data-to-parameter ratio = 16.1
Details
Open access

N-(2-Chlorophenyl)-1-(4-chlorophenyl)formamido 3-(2-nitrophenyl)propanoate

aDepartment of Laboratory Center for Medical Sciences, School of Basic Medical Sciences, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China,bJiuquan Institute for Food and Drug Control, Jiuquan 735000, Gansu Province, People's Republic of China, and cInstitute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 730000, Gansu Province, People's Republic of China
Correspondence e-mail: fanlinlan1020@163.com

In the title hydroxamic acid derivative, C22H16Cl2N2O5, the nitro-substituted benzene ring forms dihedral angles of 26.95 (15) and 87.06 (15)°, with the 4-chloro- and 2-chloro-substituted benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 68.19 (13)°. The O atoms of the nitro group were refined as disordered over two sets of sites with equal occupancies. In the crystal, weak C-H...O(=C) hydrogen bonds link molecules along [100].

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 related structures, see: Zhang et al. (2012[Zhang, H., Qu, D. & Ma, J. (2012). Acta Cryst. E68, o2904.]); Ma et al. (2012[Ma, J., Ma, Y. & He, D. (2012). Acta Cryst. E68, o3067.]).

[Scheme 1]

Experimental

Crystal data
  • C22H16Cl2N2O5

  • Mr = 459.27

  • Triclinic, [P \overline 1]

  • a = 9.1574 (8) Å

  • b = 10.1976 (6) Å

  • c = 12.1736 (8) Å

  • [alpha] = 91.847 (5)°

  • [beta] = 108.327 (8)°

  • [gamma] = 100.285 (6)°

  • V = 1057.06 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 293 K

  • 0.32 × 0.28 × 0.25 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Aglient Technologies Ltd, Yarnton, England.]) Tmin = 0.843, Tmax = 1.000

  • 7898 measured reflections

  • 4785 independent reflections

  • 3434 reflections with I > 2[sigma](I)

  • Rint = 0.018

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.139

  • S = 1.04

  • 4785 reflections

  • 298 parameters

  • 24 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O1i 0.93 2.52 3.354 (4) 150
C13-H13...O3ii 0.93 2.48 3.223 (4) 137
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Aglient Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: LH5558 ).


Acknowledgements

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

References

Agilent (2011). CrysAlis PRO. Aglient Technologies Ltd, Yarnton, England.
Ayyangark, N. R., Hrailme, C., Kalkotf, U. R. & Srinivasan, K. V. (1986). Synth. Commun. pp. 938-941.
Ma, J., Ma, Y. & He, D. (2012). Acta Cryst. E68, o3067.  [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. (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.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3498  [ doi:10.1107/S1600536812048726 ]

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