4-(2-Methyl­piperidin-1-ylcarbon­yl)pyridinium hexachloridoantimonate(V)

Bo Wang

doi:10.1107/S1600536809036587

. 2009 Sep 16;65(Pt 10):m1219. doi: 10.1107/S1600536809036587

4-(2-Methylpiperidin-1-ylcarbonyl)pyridinium hexachloridoantimonate(V)

Bo Wang ^a,^*

PMCID: PMC2970264 PMID: 21577742

Abstract

In the hexachloridoanimonate anion of the title compound, (C₁₂H₁₇N₂O)[SbCl₆], the Sb⁵⁺ion is in a slightly distorted octahedral coordination. In the 4-(2-methylpiperidine-1-carbonyl) pyridinium cation, the dihedral angle between the mean planes of the pyridine and piperzine rings is 66.3 (3)°. The mean plane of the carbonyl group is twisted by 80.5 (7)° and 42.7 (4)° relative to the mean planes of the pyridine and piperzine rings, respectively. The methyl group is in an R configuration relative to the piperidine ring which is in a slightly distorted chair conformation. The crystal packing is stabilized by N—H⋯O hydrogen bonds between cations, which form infinite zigzag chains parallel to [010].

Related literature

For the use of halogenidoantimonate salts in the study of phase transitions in dielectric–ferroelectric materials, see: Jakubas et al. (2005 ▶); Bednarska-Bolek et al. (2000 ▶). For related structures, see: Chen (2009 ▶); Clemente & Marzotto (2003 ▶); Kulicka et al. (2006 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

(C₁₂H₁₇N₂O)[SbCl₆]
M _r = 539.73
Monoclinic,
a = 8.1067 (16) Å
b = 12.700 (3) Å
c = 19.677 (4) Å
β = 99.06 (3)°
V = 2000.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.18 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.638, T _max = 0.646
17300 measured reflections
3918 independent reflections
2731 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.178
S = 1.06
3918 reflections
199 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Data collection: CrystalClear (Rigaku 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: PRPKAPPA (Ferguson, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809036587/jj2004sup1.cif

e-65-m1219-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036587/jj2004Isup2.hkl

e-65-m1219-Isup2.hkl^{(192.1KB, 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
N1—H1B⋯O1ⁱ	0.86	1.87	2.689 (9)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

Comment

Halogenidoantimonate salts are used to study phase transitions in dielectric-ferroelectric materials (Jakubas et al., 2005; Bednarska-Bolek et al., 2000). In support of this work, crystal structures of pyridinium hexachloridoantimonate, (Clemente & Marzotto, 2003),4-aminopyridinium hexachloridoantimonate (Kulicka et al., 2006) and diisonicotinium pentachloridoantimonate monohydrate (Chen, 2009) have beenreported. In continuation of our studies on halogenoantimonate salts, we report the crystal structure of the title compound, C₁₂H₁₇N2_O⁺. SbCl₆^-, (I).

In the cation (4-(2-methylpiperidine-1-carbonyl) pyridinium), the pyridine N atom is protonated. The piperidine ring (N2/C7—C11) adopts a slightly distorted chair conformation (Cremer & Pople, 1975) with puckering parameters Q, θ and φ of 0.564 (4) Å, 177.0 (6)° and 177.084 (5)°, respectively (Fig. 1). For an ideal chair θ has a value of 0 or 180°. The mean plane of the carbonyl group is twisted relative to the mean planes of the pyridine and piperzine rngs by 80.5 (7)° and 42.7 (4)°, respectively. The dihedral angle between the mean planes of pyridine and piperzine rings is 66.3 (3)°. In the anion the Sb atom is hexacoordinated with Cl atoms in a slightly distorted octahedral conformation. The Sb—Cl bond lengths (2.330 (3) to 2.348 (3) Å) are similar to that observed in pyridinium hexachlorido-antimony(V) (2.32 (1)–2.35 (5) Å; Clemente & Marzotto, 2003) and slightly shorter than that reported for 4-aminopyridinium hexachloridoantimonate (2.3608 (8)–2.3912 (7) Å; Kulicka et al.,2006). Crystal packing is stabilized by N1–H1B···O1 hydrogen bonds between cations which form infinite zigzag chains parallel to [010] (Fig. 2).

Experimental

A mixture of 4-(2-methylpiperidine-1-carbonyl)pyridine(1 mmol), SbCl₅ (1 mmol), ethanol(8 ml) and a few drops of HCl (6 mol/L) was stirred in a beaker. There were many solid powders produced and the solution was filtered. Colorless single crystals of the title compound suitable for X-ray analysis were obtained on slow evaporation of the solvents over a period of 48 h.