4-(2-Azaniumyl­eth­yl)piperazin-1-ium bis(perchlorate)

Mohammad Reza Reisi; Muhammad Saleh Salga; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536811033976

. 2011 Aug 27;67(Pt 9):o2400. doi: 10.1107/S1600536811033976

4-(2-Azaniumylethyl)piperazin-1-ium bis(perchlorate)

Mohammad Reza Reisi ^a, Muhammad Saleh Salga ^b, Hamid Khaledi ^b,^*, Hapipah Mohd Ali ^b

PMCID: PMC3200960 PMID: 22064357

Abstract

In the title compound, C₆H₁₇N₃ ²⁺·2ClO₄ ⁻, the piperazine ring adopts a chair conformation with the ethylammonium fragment occupying an equatorial position. In the crystal, the dications and perchlorate anions are linked through N—H⋯O hydrogen bonding and weak C—H⋯O hydrogen bonding into a three-dimensional supramolecular network.

Related literature

For the structures of related salts of the 4-(2-ammonioethyl)piperazin-1-ium cation, see: Guerfel et al. (1999 ▶); Srinivasan et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C₆H₁₇N₃ ²⁺·2ClO₄ ⁻
M _r = 330.13
Monoclinic,
a = 7.5218 (1) Å
b = 11.4371 (2) Å
c = 15.2239 (2) Å
β = 97.437 (1)°
V = 1298.66 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 100 K
0.28 × 0.17 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.863, T _max = 0.968
8644 measured reflections
2969 independent reflections
2671 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.080
S = 1.05
2969 reflections
187 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033976/xu5296sup1.cif

e-67-o2400-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033976/xu5296Isup2.hkl

e-67-o2400-Isup2.hkl^{(145.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033976/xu5296Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O4ⁱ	0.90 (2)	2.16 (2)	2.9298 (19)	143 (2)
N1—H1D⋯O3ⁱⁱ	0.88 (2)	2.09 (2)	2.964 (2)	168 (2)
N3—H3C⋯O6ⁱ	0.89 (2)	2.38 (2)	3.0741 (19)	135 (2)
N3—H3C⋯O4	0.89 (2)	2.39 (2)	3.0225 (19)	128 (2)
N3—H3D⋯O1ⁱⁱⁱ	0.89 (2)	2.12 (2)	2.9875 (18)	163 (2)
N3—H3E⋯O8^iv	0.88 (2)	2.14 (2)	2.9025 (19)	145 (2)
N3—H3E⋯O3	0.88 (2)	2.52 (2)	3.0724 (19)	122 (2)
C1—H1B⋯O7^v	0.99	2.56	3.407 (2)	143
C3—H3A⋯O8ⁱⁱⁱ	0.99	2.56	3.226 (2)	124
C5—H5A⋯O5^vi	0.99	2.58	3.436 (2)	145
C5—H5B⋯O2ⁱⁱⁱ	0.99	2.46	3.452 (2)	178

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

The authors thank the University of Malaya for funding this study (PPP grant No. PS359/2009C).

supplementary crystallographic information

Comment

The crystals of the title compound were obtained unexpectedly during an attempt to prepare a tin(IV) complex of 1-(2-aminoethyl)piperazine in the presence of sodium perchlorate. The organic molecule is doubly protonated at its primary and secondary N atoms, while the tertiary N atom, N2, remains unprotonated. Similar to the structures of some other 1-(2-ammoniumethyl)piperazinium salts (Guerfel et al., 1999; Srinivasan et al., 2008, 2009), the piperazine ring adopts a chair conformation with the ethylammonium group occupying an equatorial position. In the crystal, the dicationic organic moieties and perchlorate anions are linked through N—H···O and C—H···O interactions (Table 1) into a three-dimensional supra-molecular network.

Experimental

A mixture of 4-(2-aminoethyl)piperazine (0.26 g, 2 mmol) and Bu₂SnCl₂ (0.6 g, 2 mmol) in methanol (50 ml) was refluxed for 2 h. NaClO₄ (0.56 g, 4 mmol) was then added and the precipitated sodium chloride was filtered off. The filtrate was evaporated and the obtained solid was recrystallized from ethanol at room temperature to give the colorless crystals of the title compound.