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Volume 69 
Part 4 
Page o561  
April 2013  

Received 28 February 2013
Accepted 15 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.113
Data-to-parameter ratio = 16.4
Details
Open access

(4-Chlorobenzoyl)(4-chlorophenyl)amino 3-(2-nitrophenyl)propanoate

aLanzhou Maternal and Child Health Care Hospital, Lanzhou 730000, Gansu Province, People's Republic of China, and bThe Peoples First Hospital of Lanzhou, Lanzhou 730000, Gansu Province, People's Republic of China
Correspondence e-mail: shaochangjiang1020@126.com

In the title hydroxamic acid derivate, C22H16Cl2N2O5, the nitro-substituted benzene ring forms dihedral angles of 14.11 (15) and 16.08 (15)°, with the 4-chlorobenzoyl and 4-chlorophenyl benzene rings, respectively. The dihedral angle between the chloro-substituted benzene rings is 2.28 (13)°. In the crystal, molecules are linked by weak C-H...O hydrogen bonds, forming chains 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 = 6.1710 (3) Å

  • b = 12.8881 (7) Å

  • c = 13.3490 (8) Å

  • [alpha] = 89.933 (5)°

  • [beta] = 76.959 (5)°

  • [gamma] = 82.114 (4)°

  • V = 1024.03 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 294 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 = 0.757, Tmax = 1.000

  • 7506 measured reflections

  • 4578 independent reflections

  • 3269 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.113

  • S = 1.02

  • 4578 reflections

  • 280 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O1i 0.93 2.40 3.177 (2) 140
C17-H17B...O4ii 0.97 2.55 3.515 (3) 171
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, 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: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5593 ).


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.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Ma, J., Ma, Y. & He, D. (2012). Acta Cryst. E68, o3067.  [CSD] [CrossRef] [details]
Noh, E. J., Lim, D. S., Jeong, G. & Lee, J. S. (2009). Biochem. Biophys. Res. Commun. 378, 326-331.  [CrossRef] [PubMed] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [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 (2013). E69, o561  [ doi:10.1107/S1600536813007174 ]

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