20,23,26,29,32,35,38,41-Octa­oxa-5,9,13-triaza­penta­cyclo­[15.14.10.13,30.17,11.115,19]tetra­tetra­conta-1,3(42),7,9,11(44),15(43),16,18,30-nona­ene-6,12-dione acetone mono­solvate

Pan, S.; Yang, D.; Yang, Y.; Jiang, L.

doi:10.1107/S1600536811051877

Volume 68
Part 1
Page o107
January 2012

Received 5 October 2011
Accepted 1 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R = 0.056
wR = 0.172
Data-to-parameter ratio = 8.0
Details

20,23,26,29,32,35,38,41-Octaoxa-5,9,13-triazapentacyclo[15.14.10.1^3,30.1^7,11.1^15,19]tetratetraconta-1,3(42),7,9,11(44),15(43),16,18,30-nonaene-6,12-dione acetone monosolvate

Shaowu Pan,^a Dengke Yang,^a Yu Yang ^a and Lasheng Jiang ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
Correspondence e-mail: jiang6128@yahoo.com.cn

In the crystal structure of the title compound, C₃₃H₃₉N₃O₁₀·C₃H₆O, the acetone molecule is encapsulated into the cavity of the cryptand and fixed by two N-HO and one C-HO hydrogen bond. C-HO and C-HN interactions link neighbouring cryptands. The dihedral angles between the pyridine ring and the benzene rings are 86.47 (17) and 85.53 (13)°.

Related literature

Cryptands have been utilized as hosts to form supramolecular assemblies, see: Balzani et al. (2000). Crown ether-based cryptands can form more stable supramolecular complexes with paraquat, paraquat derivatives, diquat and secondary ammonium salts than the corresponding simple crown ethers by virtue of multiple non-covalent interactions, see: Huang et al. (2005). The title compound was obtained by the reaction of bis(5-aminomethyl-1,3-phenylene)-26-crown-8 (Wester & Voegtle, 1980) with pyridine-3,5-dicarbonyl dichloride (Chen et al., 2010).

Experimental

Crystal data

C₃₃H₃₉N₃O₁₀·C₃H₆O
M_r = 695.75
Tetragonal, P 4₃
a = 14.232 (3) Å
c = 17.615 (4) Å
V = 3567.8 (12) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.32 × 0.28 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.970, T_max = 0.976
19761 measured reflections
3626 independent reflections
2127 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.172
S = 1.00
3626 reflections
453 parameters
1 restraint
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.86	2.36	3.209 (7)	170
N2-H2O1	0.86	2.53	3.382 (7)	172
C9-H9O1	0.93	2.43	3.271 (7)	151
C3-H3O11ⁱ	0.93	2.46	3.356 (6)	161
C33-H33BN3ⁱⁱ	0.97	2.60	3.401 (8)	140
Symmetry codes: (i) $[-y+2, x, z-{\script{1\over 4}}]$ ; (ii) $[-y+1, x, z+{\script{3\over 4}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: AA2033 ).

Acknowledgements

The authors gratefully acknowledge the support of the National Natural Science Foundation of China (Nos. 21072066 and 20672038) and the Natural Science Foundation of Guangdong Province of China (No. 8151063101000015).

References

Balzani, V., Credi, A., Raymo, F. M. & Stoddart, J. F. (2000). Angew. Chem. Int. Ed. 39, 3348-3391.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, M. J., Han, S. J., Jiang, L. S., Zhou, S. G., Jiang, F., Xu, Z. K., Liang, J. D. & Zhang, S. H. (2010). Chem. Commun., 46, 3932-3934.
Huang, F. H., Zakharov, L. N., Rheingold, A. L., Ashraf-Khorassani, M. & Gibson, H. W. (2005). J. Org. Chem. 70, 809-813.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wester, N. & Voegtle, F. (1980). Chem. Ber. 113, 1487-1493.

organic compounds

20,23,26,29,32,35,38,41-Octaoxa-5,9,13-triazapentacyclo[15.14.10.13,30.17,11.115,19]tetratetraconta-1,3(42),7,9,11(44),15(43),16,18,30-nonaene-6,12-dione acetone monosolvate