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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o592.
Published online 2009 February 25. doi:  10.1107/S1600536809006060
PMCID: PMC2968435

Pyrrolidinium chloride

Abstract

The title compound, C4H10N+·Cl, was obtained as a decomposition product from 2,6-bis­(pyrrolidin­yl)pyridine. The anion lies on the same cristallographic mirror plane as the N atom of the cation, the complete cation being generated by mirror symmetry. The anions and cations are connected by N+—H(...)Cl hydrogen bonds into chains along [100]. The pyrrolidinium cation is puckered in an envelope conformation E N1.

Related literature

For details of the synthesis of 2,6-bis­(pyrrolidin­yl)pyridine, see: Folmer-Anderson et al. (2005 [triangle]). For related structures containing the pyrrolidinium cation, see: Kashino et al. (1978 [triangle]); Moritani et al. (1987 [triangle]); Jakubas et al. (2005 [triangle]). For a description of the E N1 conformation of the five-membered ring, see: Cremer & Pople (1975 [triangle]).

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Object name is e-65-0o592-scheme1.jpg

Experimental

Crystal data

  • C4H10N+·Cl
  • M r = 107.58
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o592-efi8.jpg
  • a = 7.4429 (4) Å
  • b = 9.4104 (5) Å
  • c = 8.9021 (4) Å
  • V = 623.51 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.48 mm−1
  • T = 200 K
  • 0.22 × 0.13 × 0.12 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: none
  • 4239 measured reflections
  • 756 independent reflections
  • 608 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.120
  • S = 1.07
  • 756 reflections
  • 31 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 2004 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006060/bi2348sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006060/bi2348Isup2.hkl

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

Acknowledgments

TK thanks the Hanns Seidel Stiftung for a personal grant funded by the German Bundesministerium für Bildung und Forschung.

supplementary crystallographic information

Comment

The title compound was obtained as a decomposition product. The organic salt is composed of the pyrrolidinium cation and a chloride anion (Fig. 1). The crystal packing is shown in Fig. 2. In the crystal, both H atoms bonded to N1 of the pyrrolidinium cation are involved in hydrogen bonds with chloride as acceptor. Both can be described according to graph set analysis with a D11(2) descriptor on the unitary level. This bonding pattern leads to chains along [1 0 0] which, starting from chloride, can be described according to graph set analysis with a C21(4) descriptor on the binary level. The hydrogen bonding pattern is shown in Fig. 3.

The Cs symmetric five-membered pyrrolidinium ring can be described according to Cremer & Pople (1975) by the puckering parameters q2 = 0.3061 Å and Φ2 = 180.0000. The closest pucker descriptor is an envelope EN1.

Experimental

The title compound was obtained as decomposition product of 2,6-bis(pyrrolidinyl)pyridine, which was synthesized according to Folmer-Anderson et al. (2005), after 4 months at room temperature.

Refinement

H atoms were placed in calculated positions (C—H = 0.99 Å, N—H = 0.92 Å) and were included in the refinement in the riding model approximation with Uiso(H) = 1.2 Ueq(C/N).

Figures

Fig. 1.
The molecular structure of the Cs symmetric title compound with anisotropic displacement ellipsoids drawn at 50% probability for non-H atoms. Symmetry code: (i) x, -y + 1/2, z.
Fig. 2.
Packing of the title compound, viewed along [0 1 0].
Fig. 3.
N—H···Cl hydrogen bonds lead to chain-like structures in the crystal structure along [1 0 0], shown here normal to [0 1 0]. Symmetry codes: (i) x + 1/2, -y + 1/2, -z + 1/2; (ii) x - 1/2, -y + 1/2, -z + 1/2; (iii) x - 1, ...

Crystal data

C4H10N+·ClF(000) = 232
Mr = 107.58Dx = 1.146 Mg m3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 2321 reflections
a = 7.4429 (4) Åθ = 3.1–27.5°
b = 9.4104 (5) ŵ = 0.48 mm1
c = 8.9021 (4) ÅT = 200 K
V = 623.51 (5) Å3Block, colourless
Z = 40.22 × 0.13 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer608 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.037
MONTEL, graded multilayered X-ray opticsθmax = 27.5°, θmin = 3.2°
[var phi] and ω scansh = −8→9
4239 measured reflectionsk = −12→12
756 independent reflectionsl = −11→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0625P)2 + 0.1854P] where P = (Fo2 + 2Fc2)/3
756 reflections(Δ/σ)max < 0.001
31 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Refinement. Hydrogen atoms were placed in calculated positions (C–H 0.99 Å for methylene C atoms and N–H 0.92 Å for N atoms) and were included in the refinement in the riding model approximation with U(H) set to 1.2 Ueq(C) for C atoms and 1.2 Ueq(N) for N atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.2072 (3)0.25000.3955 (3)0.0473 (6)
H1010.23410.25000.29460.057*
H1020.08430.25000.40650.057*
C10.3204 (4)0.1712 (3)0.6283 (3)0.0781 (8)
H110.22490.13480.69540.094*
H120.43760.13480.66410.094*
C20.2871 (3)0.1242 (2)0.4702 (3)0.0623 (6)
H210.40090.09630.42080.075*
H220.20320.04270.46770.075*
Cl10.29515 (8)0.25000.05610 (7)0.0488 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0466 (12)0.0500 (13)0.0452 (12)0.000−0.0007 (10)0.000
C10.102 (2)0.0775 (16)0.0553 (14)0.0109 (14)−0.0060 (13)0.0106 (12)
C20.0803 (16)0.0411 (11)0.0657 (14)0.0045 (10)0.0013 (11)0.0050 (9)
Cl10.0477 (4)0.0528 (4)0.0459 (4)0.000−0.0020 (3)0.000

Geometric parameters (Å, °)

N1—C2i1.482 (3)C1—C21.495 (4)
N1—C21.482 (2)C1—H110.9900
N1—H1010.9200C1—H120.9900
N1—H1020.9200C2—H210.9900
C1—C1i1.482 (5)C2—H220.9900
C2i—N1—C2105.9 (2)C1i—C1—H12110.3
C2i—N1—H101110.5C2—C1—H12110.3
C2—N1—H101110.5H11—C1—H12108.5
C2i—N1—H102110.5N1—C2—C1104.64 (19)
C2—N1—H102110.5N1—C2—H21110.8
H101—N1—H102108.7C1—C2—H21110.8
C1i—C1—C2107.20 (13)N1—C2—H22110.8
C1i—C1—H11110.3C1—C2—H22110.8
C2—C1—H11110.3H21—C2—H22108.9
C2i—N1—C2—C131.4 (3)C1i—C1—C2—N1−19.16 (18)

Symmetry codes: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H101···Cl10.922.173.091 (3)180
N1—H102···Cl1ii0.922.183.097 (2)177

Symmetry codes: (ii) x−1/2, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2348).

References

  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Folmer-Anderson, J. F., Lynch, V. M. & Anslyn, E. V. (2005). Chem. Eur. J.11, 5319–5326. [PubMed]
  • Jakubas, R., Bednarska-Bolek, B., Zaleski, J., Medycki, W., Holderna-Natkaniec, K., Zielinski, P. & Galazka, M. (2005). Solid State Sci.7, 381–390.
  • Kashino, S., Kataoka, S. & Haisa, M. (1978). Bull. Chem. Soc. Jpn, 51, 1717–1722.
  • Moritani, Y., Sasahara, N., Kashino, S. & Haisa, M. (1987). Acta Cryst. C43, 154–158.
  • Nonius (2004). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography