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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 [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.054
wR = 0.179
Data-to-parameter ratio = 14.2
Details
Open access

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

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-H...O hydrogen bonds into centrosymmetric dimers and these dimers are assembled into chains along the a-axis direction, also through N-H...O hydrogen bonds. The perchlorate anions are linked to the hydroxy groups of the cations by O-H...O 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[Li, X.-W., Jiang, M., Li, Y.-T., Wu, Z.-Y. & Yan, C.-W. (2010). J. Coord. Chem. 63, 1582-1596.]). For the synthesis, see: Tao et al. (2003[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.]).

[Scheme 1]

Experimental

Crystal data
  • C13H19ClN3O3+·ClO4-

  • Mr = 400.21

  • Monoclinic, P 21 /c

  • a = 6.7423 (5) Å

  • b = 12.8169 (10) Å

  • c = 21.6454 (17) Å

  • [beta] = 98.275 (1)°

  • V = 1851.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.823, Tmax = 0.951

  • 10727 measured reflections

  • 4204 independent reflections

  • 2526 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O5 0.89 (4) 1.80 (4) 2.693 (3) 174 (3)
N2-H2A...O2i 0.88 (3) 2.12 (3) 2.905 (3) 149 (2)
N3A-H3A...O3ii 0.91 2.04 2.814 (6) 142
N3B-H3B...O3ii 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[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [CrossRef] [ChemPort] [details]
Li, X.-W., Jiang, M., Li, Y.-T., Wu, Z.-Y. & Yan, C.-W. (2010). J. Coord. Chem. 63, 1582-1596.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
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.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o8  [ doi:10.1107/S1600536811050653 ]

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