Pyrrolidinium chloride.

The title compound, C(4)H(10)N(+)·Cl(-), was obtained as a decomposition product from 2,6-bis-(pyrrolidin-yl)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 ▶). For related structures containing the pyrrolidinium cation, see: Kashino et al. (1978 ▶); Moritani et al. (1987 ▶); Jakubas et al. (2005 ▶). For a description of the E N1 conformation of the five-membered ring, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C4H10N+·Cl−

M = 107.58

Orthorhombic,

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

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

C4H10N+·Cl−	F(000) = 232
Mr = 107.58	Dx = 1.146 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2321 reflections
a = 7.4429 (4) Å	θ = 3.1–27.5°
b = 9.4104 (5) Å	µ = 0.48 mm−1
c = 8.9021 (4) Å	T = 200 K
V = 623.51 (5) Å3	Block, colourless
Z = 4	0.22 × 0.13 × 0.12 mm

Nonius KappaCCD diffractometer	608 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.037
MONTEL, graded multilayered X-ray optics	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −8→9
4239 measured reflections	k = −12→12
756 independent reflections	l = −11→10

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

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.

	x	y	z	Uiso*/Ueq
N1	0.2072 (3)	0.2500	0.3955 (3)	0.0473 (6)
H101	0.2341	0.2500	0.2946	0.057*
H102	0.0843	0.2500	0.4065	0.057*
C1	0.3204 (4)	0.1712 (3)	0.6283 (3)	0.0781 (8)
H11	0.2249	0.1348	0.6954	0.094*
H12	0.4376	0.1348	0.6641	0.094*
C2	0.2871 (3)	0.1242 (2)	0.4702 (3)	0.0623 (6)
H21	0.4009	0.0963	0.4208	0.075*
H22	0.2032	0.0427	0.4677	0.075*
Cl1	0.29515 (8)	0.2500	0.05610 (7)	0.0488 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0466 (12)	0.0500 (13)	0.0452 (12)	0.000	−0.0007 (10)	0.000
C1	0.102 (2)	0.0775 (16)	0.0553 (14)	0.0109 (14)	−0.0060 (13)	0.0106 (12)
C2	0.0803 (16)	0.0411 (11)	0.0657 (14)	0.0045 (10)	0.0013 (11)	0.0050 (9)
Cl1	0.0477 (4)	0.0528 (4)	0.0459 (4)	0.000	−0.0020 (3)	0.000

N1—C2i	1.482 (3)	C1—C2	1.495 (4)
N1—C2	1.482 (2)	C1—H11	0.9900
N1—H101	0.9200	C1—H12	0.9900
N1—H102	0.9200	C2—H21	0.9900
C1—C1i	1.482 (5)	C2—H22	0.9900
C2i—N1—C2	105.9 (2)	C1i—C1—H12	110.3
C2i—N1—H101	110.5	C2—C1—H12	110.3
C2—N1—H101	110.5	H11—C1—H12	108.5
C2i—N1—H102	110.5	N1—C2—C1	104.64 (19)
C2—N1—H102	110.5	N1—C2—H21	110.8
H101—N1—H102	108.7	C1—C2—H21	110.8
C1i—C1—C2	107.20 (13)	N1—C2—H22	110.8
C1i—C1—H11	110.3	C1—C2—H22	110.8
C2—C1—H11	110.3	H21—C2—H22	108.9
C2i—N1—C2—C1	31.4 (3)	C1i—C1—C2—N1	−19.16 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···Cl1	0.92	2.17	3.091 (3)	180
N1—H102···Cl1ii	0.92	2.18	3.097 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H101⋯Cl1	0.92	2.17	3.091 (3)	180
N1—H102⋯Cl1i	0.92	2.18	3.097 (2)	177

Symmetry code: (i) .