(S)-2-(Pyrrolidinium-2-ylmethyl-sulfan-yl)pyridinium dibromide.

In the title compound, C(10)H(16)N(2)S(2+)·2Br(-), the pyrrolidine ring displays an envelope conformation, with the flap C atom lying 0.484 (5) Å out of the plane of the rest of the pyrrolidine ring. The thio-ether group connects the pyridine ring and the 2-methyl-pyrrolidine group. Both pyrrolidine NH bonds form hydrogen bonds to the bromide anions. These hydrogen bonds link the cations and anions in a helical chain along the c axis.

Related literature

For related literature, see: Ishii et al. (2004 ▶); Xu et al. (2007 ▶); Larson (1970 ▶).

Experimental

Crystal data

C10H16N2S2+·2Br−

M = 356.12

Trigonal,

a = 8.9892 (9) Å

c = 15.4567 (14) Å

V = 1081.66 (18) Å3

Z = 3

Mo Kα radiation

μ = 5.76 mm−1

T = 296 (1) K

0.35 × 0.30 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi,1995 ▶) T min = 0.162, T max = 0.266

10585 measured reflections

3169 independent reflections

1902 reflections with F 2 > 2.0σ(F 2)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.108

S = 1.01

3169 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.53 e Å−3

Absolute structure: Flack (1983 ▶), 1037 Friedel pairs

Flack parameter: 0.017 (2)

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008313/pk2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008313/pk2087Isup2.hkl

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

C10H16N2S2+·2Br–	Z = 3
Mr = 356.12	F000 = 528.00
Trigonal, P32	Dx = 1.640 Mg m−3
Hall symbol: P 32	Mo Kα radiation λ = 0.71073 Å
a = 8.9892 (9) Å	Cell parameters from 5169 reflections
b = 8.9892 (9) Å	θ = 3.7–27.4º
c = 15.4567 (14) Å	µ = 5.76 mm−1
α = 90º	T = 296 (1) K
β = 90º	Chunk, colorless
γ = 120º	0.35 × 0.30 × 0.23 mm
V = 1081.66 (18) Å3

Rigaku R-AXIS RAPID diffractometer	1902 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.061
ω scans	θmax = 27.4º
Absorption correction: multi-scan(ABSCOR; Higashi,1995)	h = −11→11
Tmin = 0.162, Tmax = 0.266	k = −11→10
10585 measured reflections	l = −18→20
3169 independent reflections

Refinement on F2	(Δ/σ)max = 0.013
R[F2 > 2σ(F2)] = 0.036	Δρmax = 0.67 e Å−3
wR(F2) = 0.108	Δρmin = −0.53 e Å−3
S = 1.01	Extinction correction: Larson (1970) Crystallographic Computing eq. 22
3169 reflections	Extinction coefficient: 385 (18)
138 parameters	Absolute structure: Flack (1983), 1037 Friedel Pairs
H-atom parameters constrained	Flack parameter: 0.017 (2)
w = 1/[0.7600σ(Fo2)]/(4Fo2)

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

	x	y	z	Uiso*/Ueq
Br1	0.51453 (17)	0.87503 (13)	0.16904 (9)	0.1032 (4)
Br2	0.10004 (11)	0.14553 (10)	0.04190 (9)	0.0605 (2)
S1	0.0678 (3)	0.4733 (3)	0.31433 (12)	0.0671 (7)
N1	0.4515 (9)	0.5570 (8)	0.2963 (3)	0.067 (2)
N2	0.0359 (7)	0.6865 (8)	0.2110 (3)	0.053 (2)
C1	0.3184 (9)	0.4069 (9)	0.2462 (4)	0.053 (2)
C2	0.3905 (11)	0.2858 (11)	0.2388 (5)	0.071 (3)
C3	0.5771 (13)	0.4004 (16)	0.2379 (8)	0.086 (5)
C4	0.6121 (14)	0.5513 (18)	0.2933 (7)	0.077 (5)
C5	0.1434 (10)	0.3261 (10)	0.2879 (4)	0.059 (2)
C6	0.0388 (9)	0.5412 (9)	0.2143 (4)	0.050 (2)
C7	0.0160 (10)	0.4576 (10)	0.1352 (4)	0.059 (2)
C8	−0.0040 (10)	0.5283 (11)	0.0612 (4)	0.066 (2)
C9	−0.0037 (10)	0.6817 (12)	0.0635 (4)	0.067 (2)
C10	0.0138 (10)	0.7576 (11)	0.1396 (4)	0.062 (2)
H1	0.3105	0.4460	0.1880	0.064*
H2	0.4673	0.6511	0.2735	0.080*
H3	0.4187	0.5509	0.3491	0.080*
H7	0.0144	0.3534	0.1330	0.071*
H8	−0.0180	0.4724	0.0087	0.079*
H9	−0.0154	0.7310	0.0130	0.080*
H10	0.0108	0.8593	0.1432	0.074*
H21	0.3560	0.2085	0.2879	0.085*
H22	0.3522	0.2195	0.1857	0.085*
H31	0.6169	0.4377	0.1793	0.103*
H32	0.6343	0.3421	0.2614	0.103*
H41	0.6450	0.5369	0.3511	0.092*
H42	0.7033	0.6564	0.2682	0.092*
H51	0.1477	0.2708	0.3409	0.071*
H52	0.0614	0.2403	0.2484	0.071*
H201	0.0494	0.7403	0.2590	0.064*

	U11	U22	U33	U12	U13	U23
Br1	0.1369 (10)	0.0925 (8)	0.0513 (4)	0.0357 (7)	0.0061 (5)	0.0034 (4)
Br2	0.0670 (6)	0.0510 (5)	0.0630 (4)	0.0292 (4)	0.0073 (4)	0.0054 (3)
S1	0.0848 (16)	0.0802 (16)	0.0554 (11)	0.0555 (14)	0.0125 (10)	0.0098 (10)
N1	0.072 (4)	0.063 (4)	0.053 (3)	0.026 (4)	−0.001 (3)	−0.006 (3)
N2	0.055 (4)	0.055 (4)	0.053 (3)	0.029 (3)	0.011 (2)	0.003 (2)
C1	0.052 (4)	0.046 (4)	0.058 (4)	0.022 (4)	−0.001 (3)	−0.001 (3)
C2	0.055 (5)	0.082 (6)	0.084 (5)	0.040 (5)	0.000 (4)	−0.005 (4)
C3	0.070 (8)	0.088 (10)	0.090 (14)	0.032 (7)	0.004 (7)	0.000 (10)
C4	0.061 (7)	0.083 (14)	0.093 (10)	0.041 (9)	−0.004 (6)	−0.003 (10)
C5	0.051 (5)	0.063 (5)	0.065 (5)	0.030 (4)	0.011 (3)	0.009 (3)
C6	0.056 (5)	0.041 (4)	0.060 (4)	0.030 (4)	0.008 (3)	−0.003 (3)
C7	0.075 (5)	0.056 (5)	0.055 (4)	0.040 (4)	0.002 (3)	0.002 (3)
C8	0.071 (6)	0.078 (6)	0.053 (4)	0.041 (5)	0.001 (3)	0.001 (4)
C9	0.077 (6)	0.082 (6)	0.053 (4)	0.049 (5)	−0.002 (3)	0.002 (4)
C10	0.088 (6)	0.061 (5)	0.050 (4)	0.048 (5)	0.002 (3)	0.009 (3)

S1—C5	1.811 (11)	N1—H3	0.860
S1—C6	1.729 (7)	N2—H201	0.860
N1—C1	1.496 (8)	C1—H1	0.980
N1—C4	1.471 (18)	C2—H21	0.970
N2—C6	1.321 (12)	C2—H22	0.970
N2—C10	1.339 (10)	C3—H31	0.970
C1—C2	1.524 (16)	C3—H32	0.970
C1—C5	1.508 (10)	C4—H41	0.970
C2—C3	1.465 (12)	C4—H42	0.970
C3—C4	1.499 (9)	C5—H51	0.970
C6—C7	1.396 (9)	C5—H52	0.970
C7—C8	1.363 (12)	C7—H7	0.930
C8—C9	1.379 (16)	C8—H8	0.930
C9—C10	1.329 (10)	C9—H9	0.930
N1—H2	0.860	C10—H10	0.930
C5—S1—C6	103.5 (4)	C1—C2—H22	110.8
C1—N1—C4	108.0 (8)	C3—C2—H21	110.8
C6—N2—C10	125.8 (6)	C3—C2—H22	110.8
N1—C1—C2	104.4 (7)	H21—C2—H22	109.5
N1—C1—C5	112.6 (6)	C2—C3—H31	110.3
C2—C1—C5	113.7 (6)	C2—C3—H32	110.3
C1—C2—C3	104.2 (8)	C4—C3—H31	110.3
C2—C3—C4	106.2 (11)	C4—C3—H32	110.3
N1—C4—C3	106.5 (8)	H31—C3—H32	109.5
S1—C5—C1	115.3 (6)	N1—C4—H41	110.2
S1—C6—N2	117.7 (5)	N1—C4—H42	110.2
S1—C6—C7	126.9 (7)	C3—C4—H41	110.2
N2—C6—C7	115.4 (7)	C3—C4—H42	110.2
C6—C7—C8	120.2 (9)	H41—C4—H42	109.5
C7—C8—C9	120.7 (7)	S1—C5—H51	108.0
C8—C9—C10	118.4 (8)	S1—C5—H52	108.0
N2—C10—C9	119.5 (10)	C1—C5—H51	108.0
C1—N1—H2	109.8	C1—C5—H52	108.0
C1—N1—H3	109.8	H51—C5—H52	109.5
C4—N1—H2	109.8	C6—C7—H7	119.9
C4—N1—H3	109.8	C8—C7—H7	119.9
H2—N1—H3	109.5	C7—C8—H8	119.7
C6—N2—H201	117.1	C9—C8—H8	119.7
C10—N2—H201	117.1	C8—C9—H9	120.8
N1—C1—H1	108.7	C10—C9—H9	120.8
C2—C1—H1	108.7	N2—C10—H10	120.2
C5—C1—H1	108.7	C9—C10—H10	120.2
C1—C2—H21	110.8
C5—S1—C6—N2	−159.4 (5)	N1—C1—C5—S1	51.7 (8)
C5—S1—C6—C7	21.3 (8)	C2—C1—C5—S1	170.2 (5)
C6—S1—C5—C1	66.8 (5)	C5—C1—C2—C3	−153.7 (7)
C1—N1—C4—C3	2.2 (10)	C1—C2—C3—C4	32.4 (11)
C4—N1—C1—C2	17.3 (7)	C2—C3—C4—N1	−22.0 (12)
C4—N1—C1—C5	141.1 (8)	S1—C6—C7—C8	−179.4 (6)
C6—N2—C10—C9	−1.5 (12)	N2—C6—C7—C8	1.2 (11)
C10—N2—C6—S1	−179.6 (5)	C6—C7—C8—C9	−0.6 (10)
C10—N2—C6—C7	−0.1 (9)	C7—C8—C9—C10	−1.0 (12)
N1—C1—C2—C3	−30.6 (8)	C8—C9—C10—N2	2.1 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···Br1	0.86	2.45	3.278 (7)	163
N1—H3···Br1i	0.86	2.43	3.271 (5)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯Br1	0.86	2.45	3.278 (7)	163
N1—H3⋯Br1i	0.86	2.43	3.271 (5)	165

Symmetry code: (i) .