2,4,5-Trichloro­anilinium perchlorate 18-crown-6 clathrate

Xu, J.

doi:10.1107/S1600536812006162

Volume 68
Part 3
Page o739
March 2012

Received 4 February 2012
Accepted 12 February 2012
Online 17 February 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
Disorder in solvent or counterion
R = 0.054
wR = 0.152
Data-to-parameter ratio = 13.6
Details

2,4,5-Trichloroanilinium perchlorate 18-crown-6 clathrate

Jie Xu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: chemcrystal66@yahoo.com.cn

In the title compound, C₆H₅Cl₃N⁺·ClO₄^-·C₁₂H₂₄O₆, the perchlorate anion is disordered over two orientations in a 0.666 (17):0.334 (17) ratio. The ammonium group of the organic cation inserts into the crown ether ring and forms three bifurcated N-H(O,O) hydrogen bonds to generate a supramolecular complex. The macrocycle has approximate D_3d local symmetry.

Related literature

For background to molecular ferroelectric materials, see: Fu et al. (2011).

Experimental

Crystal data

C₆H₅Cl₃N⁺·ClO₄^-·C₁₂H₂₄O₆
M_r = 561.22
Triclinic, $[P \overline 1]$
a = 9.4961 (19) Å
b = 11.783 (2) Å
c = 11.852 (2) Å
= 97.86 (3)°
= 90.39 (3)°
= 105.26 (3)°
V = 1266.1 (4) Å³
Z = 2
Mo K radiation
= 0.52 mm^-1
T = 298 K
0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 (2 × 2 bin mode) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.910, T_max = 1.000
11310 measured reflections
4713 independent reflections
3562 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.152
S = 1.03
4713 reflections
346 parameters
18 restraints
H-atom parameters constrained
_max = 0.57 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1CO1ⁱ	0.89	2.13	2.916 (3)	147
N1-H1CO6ⁱ	0.89	2.21	2.899 (3)	134
N1-H1DO5ⁱ	0.89	2.06	2.896 (3)	156
N1-H1DO4ⁱ	0.89	2.52	3.052 (3)	119
N1-H1EO3ⁱ	0.89	2.19	3.046 (3)	161
N1-H1EO2ⁱ	0.89	2.35	2.856 (3)	116
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6625 ).

Acknowledgements

This work was supported by a Start-up Grant of Southeast University, China.

References

Fu, D.-W., Zhang, W., Cai, H.-L., Ge, J.-Z., Zhang, Y. & Xiong, R.-G. (2011). Adv. Mater. 23, 5658-5662.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds