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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 [sigma](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
Open access

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

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-H...N 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-H...O and O-H...O 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[Formica, M., Fusi, V., Giorgi, L. & Micheloni, M. (2012). Coord. Chem. Rev. 256, 170-192.]); Wang et al. (1998[Wang, S., Zheng, S. P., Meng, H. & Hua, W. T. (1998). Synth. Met. 93, 181-185.]). For systems able to recognise and signal metal cations and anions, see: Ambrosi et al. (2006[Ambrosi, G., Dapporto, P., Formica, M., Fusi, V., Giorgi, L., Guerri, A., Micheloni, M., Paoli, P., Pontellini, R. & Rossi, P. (2006). Inorg. Chem. 45, 304-314.], 2011[Ambrosi, G., Formica, M., Fusi, V., Giorgi, L., Macedi, E., Micheloni, M., Paoli, P., Pontellini, R. & Rossi, P. (2011). Chem. Eur. J. 17, 1670-1682.]); Ambrosi, Formica, Fusi, Giorgi, Macedi, Micheloni, Paoli et al. (2010[Ambrosi, G., Formica, M., Fusi, V., Giorgi, L., Macedi, E., Micheloni, M., Paoli, P., Pontellini, R. & Rossi, P. (2010). Inorg Chem. 48, 9940-9948.]); Ambrosi, Formica, Fusi, Giorgi, Macedi, Micheloni, Piersanti et al. (2010[Ambrosi, G., Formica, M., Fusi, V., Giorgi, L., Macedi, E., Micheloni, M., Piersanti, G. & Pontellini, R. (2010). Org. Biomol. Chem. 8, 1471-1478.]); Bencini et al. (1994[Bencini, A., Bianchi, A., Dapporto, P., Paoli, P., Burguete, M., Doménech, A., Garcia, E., Luis, S. & Ramirez, J. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 569-577.]); Formica et al. (2008[Formica, M., Fusi, V., Paoli, P., Piersanti, P., Rossi, P., Zappia, G. & Orlando, P. (2008). New J. Chem. 32, 1204-1214.]); Terenzi et al. (2012[Terenzi, A., Fanelli, M., Ambrosi, G., Amatori, S., Fusi, V., Giorgi, L., Turco Liveri, V. & Barone, G. (2012). Dalton Trans. 41, 4389-4395.]).

[Scheme 1]

Experimental

Crystal data
  • C36H66N8O6+·6ClO4-·1.5H2O

  • Mr = 1250.69

  • Monoclinic, C 2/c

  • a = 19.5601 (7) Å

  • b = 25.0825 (8) Å

  • c = 24.2277 (9) Å

  • [beta] = 113.695 (5)°

  • V = 10884.4 (7) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 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.]) Tmin = 0.728, Tmax = 0.895

  • 30246 measured reflections

  • 10465 independent reflections

  • 6531 reflections with I > 2[sigma](I)

  • Rint = 0.056

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 1.48 e Å-3

  • [Delta][rho]min = -0.86 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...N2 0.93 1.90 2.714 (5) 145
N6-H6...N1 0.93 2.04 2.779 (6) 136
N5-H5...O1W 0.93 1.85 2.747 (6) 160
N4-H4...O2W 0.93 1.95 2.83 (1) 156
N4-H4...O2Wi 0.93 2.30 2.97 (1) 129
O1W-H1WA...O23ii 0.84 (3) 2.05 (3) 2.852 (7) 160 (3)
O1W-H1WB...O21iii 0.83 (3) 2.06 (3) 2.876 (5) 169 (3)
N7-H7...O22 0.93 2.26 3.000 (6) 137
N7-H7...O73 0.93 2.28 2.94 (1) 127
N8-H8...O42 0.93 2.27 3.09 (1) 146
N8-H8...O41iv 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[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: PARST97 (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]).


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

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Ambrosi, G., Dapporto, P., Formica, M., Fusi, V., Giorgi, L., Guerri, A., Micheloni, M., Paoli, P., Pontellini, R. & Rossi, P. (2006). Inorg. Chem. 45, 304-314.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Ambrosi, G., Formica, M., Fusi, V., Giorgi, L., Macedi, E., Micheloni, M., Paoli, P., Pontellini, R. & Rossi, P. (2010). Inorg Chem. 48, 9940-9948.  [CSD] [CrossRef]
Ambrosi, G., Formica, M., Fusi, V., Giorgi, L., Macedi, E., Micheloni, M., Paoli, P., Pontellini, R. & Rossi, P. (2011). Chem. Eur. J. 17, 1670-1682.  [CSD] [CrossRef] [ChemPort] [PubMed]
Ambrosi, G., Formica, M., Fusi, V., Giorgi, L., Macedi, E., Micheloni, M., Piersanti, G. & Pontellini, R. (2010). Org. Biomol. Chem. 8, 1471-1478.  [CrossRef] [ChemPort] [PubMed]
Bencini, A., Bianchi, A., Dapporto, P., Paoli, P., Burguete, M., Doménech, A., Garcia, E., Luis, S. & Ramirez, J. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 569-577.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Formica, M., Fusi, V., Giorgi, L. & Micheloni, M. (2012). Coord. Chem. Rev. 256, 170-192.  [ISI] [CrossRef] [ChemPort]
Formica, M., Fusi, V., Paoli, P., Piersanti, P., Rossi, P., Zappia, G. & Orlando, P. (2008). New J. Chem. 32, 1204-1214.  [ISI] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Terenzi, A., Fanelli, M., Ambrosi, G., Amatori, S., Fusi, V., Giorgi, L., Turco Liveri, V. & Barone, G. (2012). Dalton Trans. 41, 4389-4395.  [CrossRef] [ChemPort] [PubMed]
Wang, S., Zheng, S. P., Meng, H. & Hua, W. T. (1998). Synth. Met. 93, 181-185.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3453-o3454   [ doi:10.1107/S1600536812047484 ]

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