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

Fan, L.-L.; Wang, H.; Ma, J.; Shi, X.-X.

doi:10.1107/S1600536812048726

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.055
wR = 0.139
Data-to-parameter ratio = 16.1
Details

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

Lin-Lan Fan,^a ^* Hui Wang,^b Jing Ma ^c and Xiu-Xiao Shi ^c

^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-HO(=C) hydrogen bonds link molecules along [100].

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 related structures, see: Zhang et al. (2012); Ma et al. (2012).

Experimental

Crystal data

C₂₂H₁₆Cl₂N₂O₅
M_r = 459.27
Triclinic, $[P \overline 1]$
a = 9.1574 (8) Å
b = 10.1976 (6) Å
c = 12.1736 (8) Å
= 91.847 (5)°
= 108.327 (8)°
= 100.285 (6)°
V = 1057.06 (13) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.843, T_max = 1.000
7898 measured reflections
4785 independent reflections
3434 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.139
S = 1.04
4785 reflections
298 parameters
24 restraints
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O1ⁱ	0.93	2.52	3.354 (4)	150
C13-H13O3ⁱⁱ	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 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.
Noh, E. J., Lim, D. S., Jeong, G. & Lee, J. S. (2009). Biochem. Biophys. Res. Commun. 378, 326-331.
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