2,5-Bis[2-({bis­[3-(dimethyl­aza­nium­yl)prop­yl]aza­nium­yl}meth­yl)phen­yl]-1,3,4-oxadiazole hexa­kis­(perchlorate) sesquihydrate

Fusi, V.; Formica, M.; Macedi, E.; Paoli, P.; Rossi, P.

doi:10.1107/S1600536812047484

Volume 68
Part 12
Pages o3453-o3454
December 2012

Received 26 September 2012
Accepted 19 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.007 Å
H completeness 99%
Disorder in solvent or counterion
R = 0.070
wR = 0.219
Data-to-parameter ratio = 15.1
Details

2,5-Bis[2-({bis[3-(dimethylazaniumyl)propyl]azaniumyl}methyl)phenyl]-1,3,4-oxadiazole hexakis(perchlorate) sesquihydrate

Vieri Fusi,^a Mauro Formica,^a Eleonora Macedi,^b Paola Paoli ^b ^* and Patrizia Rossi ^b

^aDepartment of Basic Sciences and Fundamentals, University of Urbino, I-61029 Urbino, Italy, and ^bDipartimento Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
Correspondence e-mail: paolapaoli@unifi.it

In the title hydrated salt, C₃₆H₆₆N₈O⁶⁺·6ClO₄^-·1.5H₂O, the asymmetric unit consists of a hexaprotonated [H₆L]⁶⁺ cation, five perchlorate anions in general positions, two on twofold rotation axes (one of which is disordered), and two water molecules of crystallization in general positions, one of them disordered around a twofold crystallographic axis. In the [H₆L]⁶⁺ cation, two strong intramolecular N-HN hydrogen bonds occur, involving the N atoms of the oxadiazole ring as acceptors and the closest NH⁺ groups of each dipropylenetriamine unit. In the crystal, the [H₆L]⁶⁺ cations form channels along the a-axis direction, in which the perchlorate counter-ions and the water molecules are lodged. The crystal packing features a network of N-HO and O-HO hydrogen bonds involving the NH⁺ groups of the [H₆L]⁶⁺ cation, the perchlorate anions and the water molecules.

Related literature

For 2,5 bis[2 (chloromethyl)phenyl][1,3,4]oxadiazole, see: Formica et al. (2012); Wang et al. (1998). For systems able to recognise and signal metal cations and anions, see: Ambrosi et al. (2006, 2011); Ambrosi, Formica, Fusi, Giorgi, Macedi, Micheloni, Paoli et al. (2010); Ambrosi, Formica, Fusi, Giorgi, Macedi, Micheloni, Piersanti et al. (2010); Bencini et al. (1994); Formica et al. (2008); Terenzi et al. (2012).

Experimental

Crystal data

C₃₆H₆₆N₈O⁶⁺·6ClO₄^-·1.5H₂O
M_r = 1250.69
Monoclinic, C 2/c
a = 19.5601 (7) Å
b = 25.0825 (8) Å
c = 24.2277 (9) Å
= 113.695 (5)°
V = 10884.4 (7) Å³
Z = 8
Cu K radiation
= 3.69 mm^-1
T = 150 K
0.10 × 0.08 × 0.03 mm

Data collection

Oxford XcaliburPX diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.728, T_max = 0.895
30246 measured reflections
10465 independent reflections
6531 reflections with I > 2(I)
R_int = 0.056

Refinement

R[F² > 2(F²)] = 0.070
wR(F²) = 0.219
S = 1.06
10465 reflections
692 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 1.48 e Å^-3
_min = -0.86 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3N2	0.93	1.90	2.714 (5)	145
N6-H6N1	0.93	2.04	2.779 (6)	136
N5-H5O1W	0.93	1.85	2.747 (6)	160
N4-H4O2W	0.93	1.95	2.83 (1)	156
N4-H4O2Wⁱ	0.93	2.30	2.97 (1)	129
O1W-H1WAO23ⁱⁱ	0.84 (3)	2.05 (3)	2.852 (7)	160 (3)
O1W-H1WBO21ⁱⁱⁱ	0.83 (3)	2.06 (3)	2.876 (5)	169 (3)
N7-H7O22	0.93	2.26	3.000 (6)	137
N7-H7O73	0.93	2.28	2.94 (1)	127
N8-H8O42	0.93	2.27	3.09 (1)	146
N8-H8O41^iv	0.93	2.36	3.10 (1)	137
Symmetry codes: (i) $[-x+2, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PARST97 (Nardelli, 1995).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2084 ).

Acknowledgements

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze) where the data collection was performed.

References

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organic compounds