4-Methyl­anilinium perchlorate 18-crown-6 clathrate

Wang, Y.-F.

doi:10.1107/S1600536811053992

Volume 68
Part 1
Page o185
January 2012

Received 5 November 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.131
Data-to-parameter ratio = 18.2
Details

4-Methylanilinium perchlorate 18-crown-6 clathrate

Yu-Feng Wang ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: wangyufeng0924@163.com

In the title compound, C₇H₁₀N⁺·ClO₄^-·C₁₂H₂₄O₆, the 4-methylanilinium cation interacts with an 18-crown-6 molecule forming a rotator-stator-like structure through bifurcated N-H(O,O) hydrogen bonds between the ammonium group of the cation and the O atoms of the crown ether molecule. All three components of the structure possess mirror symmetry. The benzene ring is inclined to the mean plane of the crown ether molecule by 86.84 (8)°.

Related literature

The crystal structure of related 4-methylanilinium tetrafluoroborate 18-crown-6 clathrate has been reported by Ge & Zhao (2010).

Experimental

Crystal data

C₇H₁₀N⁺·ClO₄^-·C₁₂H₂₄O₆
M_r = 471.92
Orthorhombic, P n m a
a = 15.510 (3) Å
b = 11.717 (2) Å
c = 13.014 (3) Å
V = 2365.0 (8) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 293 K
0.27 × 0.26 × 0.23 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.944, T_max = 0.952
23471 measured reflections
2843 independent reflections
2051 reflections with I > 2(I)
R_int = 0.056

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.131
S = 1.04
2843 reflections
156 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BO2ⁱ	0.89	2.23	2.9477 (19)	138
N1-H1BO3ⁱ	0.89	2.19	2.9511 (18)	143
N1-H1CO4	0.89	2.20	2.924 (3)	138
N1-H1CO3	0.89	2.20	2.9511 (18)	142
N1-H1AO2	0.89	2.22	2.9477 (19)	139
N1-H1AO1	0.89	2.15	2.888 (3)	140
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z]$ .

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: CV5196 ).

Acknowledgements

The author thanks the SEU research start-up capital of new teachers for support.

References

Ge, J.-Z. & Zhao, M.-M. (2010). Acta Cryst. E66, m739.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds