(3-{[N-(5-Chloro-2-hy­droxy­phen­yl)oxamo­yl]amino}­prop­yl)dimethyl­aza­nium perchlorate

Yue, X.-T.; Li, X.-W.; Wu, Z.-Y.

doi:10.1107/S1600536811050653

Volume 68
Part 1
Page o8
January 2012

Received 3 November 2011
Accepted 25 November 2011
Online 3 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.054
wR = 0.179
Data-to-parameter ratio = 14.2
Details

(3-{[N-(5-Chloro-2-hydroxyphenyl)oxamoyl]amino}propyl)dimethylazanium perchlorate

Xi-Teng Yue,^a Xiao-Wen Li ^b and Zhi-Yong Wu ^b ^*

^aCollege of Feixian, Linyi University, 273400 Linyi, Shandong, People's Republic of China, and ^bMarine Drug and Food Institute, Ocean University of China, 266003 Qingdao, People's Republic of China
Correspondence e-mail: zd_wzy@hotmail.com

In the title compound, C₁₃H₁₉ClN₃O₃⁺·ClO₄^-, the 3-(dimethylammonio)propyl group of the cation is disordered over two sets of sites with occupancies 0.772 (6) and 0.228 (6). The cations are joined by pairs of N-HO hydrogen bonds into centrosymmetric dimers and these dimers are assembled into chains along the a-axis direction, also through N-HO hydrogen bonds. The perchlorate anions are linked to the hydroxy groups of the cations by O-HO hydrogen bonds. The positively charged ammonium groups and the anions give rise to folded layers parallel to the ab plane.

Related literature

For DNA binding of oxamide complexes, see: Li et al. (2010). For the synthesis, see: Tao et al. (2003).

Experimental

Crystal data

C₁₃H₁₉ClN₃O₃⁺·ClO₄^-
M_r = 400.21
Monoclinic, P 2₁ /c
a = 6.7423 (5) Å
b = 12.8169 (10) Å
c = 21.6454 (17) Å
= 98.275 (1)°
V = 1851.0 (2) Å³
Z = 4
Mo K radiation
= 0.39 mm^-1
T = 296 K
0.52 × 0.28 × 0.13 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.823, T_max = 0.951
10727 measured reflections
4204 independent reflections
2526 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.179
S = 1.03
4204 reflections
297 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.56 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O5	0.89 (4)	1.80 (4)	2.693 (3)	174 (3)
N2-H2AO2ⁱ	0.88 (3)	2.12 (3)	2.905 (3)	149 (2)
N3A-H3AO3ⁱⁱ	0.91	2.04	2.814 (6)	142
N3B-H3BO3ⁱⁱ	0.91	2.13	2.905 (18)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2031 ).

Acknowledgements

This project was supported by the Natural Science Foundation of China (No. 21071133) and the Natural Science Foundation of Qingdao City (No. 09-1-3-73-jch)

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Li, X.-W., Jiang, M., Li, Y.-T., Wu, Z.-Y. & Yan, C.-W. (2010). J. Coord. Chem. 63, 1582-1596.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tao, R.-J., Zang, S.-Q., Mei, C.-Z., Wang, Q.-L., Lou, B.-Y., Niu, J.-Y., Cheng, Y.-X. & Liao, D.-Z. (2003). J. Cluster Sci. 14, 459-469.

organic compounds