4,4′-(Propane-1,3-di­yl)dipiperidinium sulfate monohydrate

E Yang; Xu-Chun Song; Rong-Qiang Zhuang

doi:10.1107/S1600536808025300

. 2008 Aug 16;64(Pt 9):o1763. doi: 10.1107/S1600536808025300

4,4′-(Propane-1,3-diyl)dipiperidinium sulfate monohydrate

E Yang ^a,^*, Xu-Chun Song ^a, Rong-Qiang Zhuang ^b

PMCID: PMC2960564 PMID: 21201745

Abstract

In the title compound, C₁₃H₂₈N₂ ²⁺·SO₄ ²⁻·H₂O, extensive hydrogen-bonding interactions between the protonated 4,4′-(propane-1,3-diyl)dipiperidinium ions, the sulfate anions and the water molecules lead to a three-dimensional pillared and layered structure with the 4,4′-(propane-1,3-diyl)dipiperidinium ions acting as the pillars.

Experimental

Crystal data

C₁₃H₂₈N₂ ²⁺·SO₄ ²⁻·H₂O
M _r = 326.45
Monoclinic,
a = 6.2019 (2) Å
b = 22.5110 (5) Å
c = 12.0052 (3) Å
β = 100.439 (2)°
V = 1648.32 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.22 × 0.14 × 0.09 mm

Data collection

Siemens SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.927, T _max = 0.98
13022 measured reflections
2932 independent reflections
2011 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.131
S = 1.03
2932 reflections
202 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Bergerhoff et al., 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808025300/fj2138sup1.cif

e-64-o1763-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025300/fj2138Isup2.hkl

e-64-o1763-Isup2.hkl^{(143.9KB, hkl)}

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
O1W—H1WA⋯O4ⁱ	0.85	1.98	2.819 (3)	168
O1W—H1WB⋯O3ⁱⁱ	0.85	1.97	2.799 (3)	165
N1—H1NA⋯O4ⁱⁱⁱ	0.94 (3)	2.09 (3)	2.904 (3)	144 (3)
N1—H1NB⋯O3^iv	0.85 (3)	1.91 (3)	2.711 (3)	157 (3)
N2—H2NA⋯O1^v	0.88 (3)	1.83 (3)	2.704 (3)	177 (3)
N2—H2NB⋯O4^vi	0.92 (3)	2.02 (3)	2.845 (4)	149 (3)

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

Acknowledgments

The authors acknowledge financial support from the Natural Science Foundation of Fujian Province (2006 F3042).

supplementary crystallographic information

Comment

The asymmetric unit of the title compound, (I), consists of one protonated 4,4'-(propane-1,3-diyl)dipiperidinium ion, one deprotonated sulfate anion and one water molecule (Figure 1). Both protonated N ends of the 4,4'-(propane-1,3-diyl)dipiperidinium ion form N—H···O hydrogen bonds with the sulfate anion, as well as the water molecules form O—H···O hydrogen bonds with the sulfate anion, which leads to the formation of two-dimensional hydrogen-bonding layer parallel to the ac plane (Table 1 & Figure 2). The resulting layers are further pillared by the 4,4'-(propane-1,3-diyl)dipiperidinium ions to complete the three-dimensional structure.

Experimental

A solution of 4,4-trimethylenedipiperidine (1 mmol), sulfuric acid (1 mmol) and H₂O (10 ml) was slowly evaporated at room temperature, giving colorless single crystals suitable for X-ray analysis.