(S)-2-Amino-1-(pyrrolidinium-2-ylmeth-yl)pyridinium dibromide.

In the title compound, C(10)H(17)N(3) (2+)·2Br(-), the pyrrolidinium ring displays an envelope conformation, with the flap N atom lying 0.564 (6) Å from the mean plane of the remaining four C atoms. The attached methyl-ene C atom, which connects the pyrrolidinium ring and the 2-amino-pyridine group, is displaced from the plane of the four pyrrolidinium C atoms by 0.811 (8) Å in the same direction as the pyrrolidinium N atom. The amine N lies on the opposite side of this plane.

Related literature

The synthesis of (S)-(+)-2-bromo­methyl­pyrrolidine hydro­bromide is described by Xu et al. (2006 ▶). For related literature, see: Ishii et al. (2004 ▶); Larson (1970 ▶).

Experimental

Crystal data

C10H17N3 2+·2Br−

M = 339.07

Monoclinic,

a = 10.5509 (5) Å

b = 6.1755 (3) Å

c = 10.8474 (6) Å

β = 107.4830 (14)°

V = 674.14 (6) Å3

Z = 2

Mo Kα radiation

μ = 6.01 mm−1

T = 296 (1) K

0.37 × 0.32 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.110, T max = 0.458

6601 measured reflections

2681 independent reflections

1943 reflections with F 2 > 2σ(F 2)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.01

2681 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.61 e Å−3

Absolute structure: Flack (1983 ▶), with 1013 Friedel pairs

Flack parameter: 0.002 (5)

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001128/cs2067sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001128/cs2067Isup2.hkl

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

C10H17N32+·2Br–	F000 = 336.00
Mr = 339.07	Dx = 1.670 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71075 Å
Hall symbol: P 2yb	Cell parameters from 5483 reflections
a = 10.5509 (5) Å	θ = 3.2–27.5º
b = 6.1755 (3) Å	µ = 6.01 mm−1
c = 10.8474 (6) Å	T = 296 (1) K
β = 107.4830 (14)º	Platelet, colorless
V = 674.14 (6) Å3	0.37 × 0.32 × 0.13 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	1943 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.052
ω scans	θmax = 27.5º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.110, Tmax = 0.458	k = −7→8
6601 measured reflections	l = −14→14
2681 independent reflections

Refinement on F2	(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.034	Δρmax = 0.41 e Å−3
wR(F2) = 0.094	Δρmin = −0.61 e Å−3
S = 1.01	Extinction correction: Larson (1970), equation 22
2681 reflections	Extinction coefficient: 48 (6)
138 parameters	Absolute structure: Flack (1983), 1013 Friedel pairs
H-atom parameters constrained	Flack parameter: 0.002 (5)
w = 1/[0.9800σ(Fo2)]/(4Fo2)

	x	y	z	Uiso*/Ueq
Br1	0.12426 (6)	0.7373 (2)	0.07481 (6)	0.0544 (2)
Br2	0.36075 (6)	0.4571 (2)	0.62553 (6)	0.0481 (2)
N1	0.2124 (4)	0.2325 (8)	0.0528 (4)	0.0394 (13)
N2	0.2014 (4)	0.1711 (7)	0.3238 (4)	0.0383 (14)
N3	0.3461 (4)	−0.1049 (8)	0.4252 (5)	0.0504 (17)
C1	0.3320 (5)	0.2156 (10)	0.1669 (5)	0.0373 (16)
C2	0.4356 (6)	0.3574 (10)	0.1293 (7)	0.050 (2)
C3	0.3902 (8)	0.3654 (13)	−0.0157 (8)	0.072 (3)
C4	0.2652 (7)	0.2334 (12)	−0.0600 (6)	0.058 (2)
C5	0.3056 (6)	0.2905 (8)	0.2915 (6)	0.0396 (19)
C6	0.0744 (6)	0.2588 (11)	0.2846 (6)	0.0473 (19)
C7	−0.0286 (6)	0.1613 (11)	0.3117 (7)	0.058 (2)
C8	−0.0044 (5)	−0.0355 (14)	0.3828 (6)	0.054 (2)
C9	0.1193 (6)	−0.1204 (10)	0.4205 (6)	0.048 (2)
C10	0.2260 (5)	−0.0171 (10)	0.3902 (5)	0.0399 (16)
H5	0.3628	0.0650	0.1770	0.045*
H6	0.0599	0.3881	0.2384	0.057*
H7	−0.1133	0.2214	0.2845	0.070*
H8	−0.0734	−0.1056	0.4033	0.065*
H9	0.1347	−0.2491	0.4671	0.057*
H21	0.4378	0.5019	0.1650	0.060*
H22	0.5232	0.2927	0.1605	0.060*
H31	0.3725	0.5138	−0.0450	0.087*
H32	0.4578	0.3046	−0.0494	0.087*
H41	0.2847	0.0872	−0.0817	0.070*
H42	0.2022	0.2998	−0.1346	0.070*
H51	0.3871	0.2743	0.3622	0.048*
H52	0.2804	0.4420	0.2820	0.048*
H111	0.1698	0.3502	0.0555	0.047*
H112	0.1607	0.1234	0.0491	0.047*
H301	0.4104	−0.0412	0.4065	0.061*
H302	0.3597	−0.2257	0.4666	0.061*

	U11	U22	U33	U12	U13	U23
Br1	0.0568 (4)	0.0313 (3)	0.0617 (4)	0.0003 (3)	−0.0024 (3)	0.0000 (3)
Br2	0.0345 (3)	0.0652 (4)	0.0452 (4)	−0.0024 (3)	0.0130 (2)	0.0014 (3)
N1	0.035 (2)	0.038 (2)	0.044 (3)	0.003 (2)	0.011 (2)	0.000 (2)
N2	0.035 (2)	0.047 (3)	0.036 (3)	0.005 (2)	0.014 (2)	0.000 (2)
N3	0.031 (2)	0.060 (3)	0.063 (4)	0.008 (2)	0.017 (2)	0.015 (2)
C1	0.030 (2)	0.042 (3)	0.043 (3)	0.001 (2)	0.015 (2)	0.008 (2)
C2	0.047 (4)	0.057 (4)	0.048 (4)	−0.004 (3)	0.017 (3)	0.007 (3)
C3	0.070 (5)	0.088 (6)	0.065 (6)	0.003 (4)	0.030 (4)	0.016 (4)
C4	0.075 (4)	0.071 (4)	0.032 (3)	0.012 (5)	0.022 (3)	−0.003 (3)
C5	0.044 (3)	0.040 (4)	0.035 (3)	−0.002 (2)	0.013 (3)	0.002 (2)
C6	0.050 (3)	0.053 (3)	0.039 (3)	0.009 (3)	0.013 (3)	0.006 (3)
C7	0.034 (3)	0.084 (5)	0.057 (4)	0.004 (3)	0.015 (3)	−0.004 (3)
C8	0.029 (2)	0.088 (5)	0.052 (4)	0.006 (4)	0.023 (2)	−0.001 (4)
C9	0.041 (3)	0.064 (5)	0.042 (4)	−0.004 (3)	0.018 (3)	0.004 (2)
C10	0.031 (2)	0.047 (3)	0.039 (3)	0.003 (3)	0.008 (2)	−0.003 (3)

N1—C1	1.483 (6)	N3—H301	0.860
N1—C4	1.490 (9)	N3—H302	0.860
N2—C5	1.451 (8)	C1—H5	0.980
N2—C6	1.388 (8)	C2—H21	0.970
N2—C10	1.351 (7)	C2—H22	0.970
N3—C10	1.325 (7)	C3—H31	0.970
C1—C2	1.547 (9)	C3—H32	0.970
C1—C5	1.532 (9)	C4—H41	0.970
C2—C3	1.501 (9)	C4—H42	0.970
C3—C4	1.501 (9)	C5—H51	0.970
C6—C7	1.350 (9)	C5—H52	0.970
C7—C8	1.421 (9)	C6—H6	0.930
C8—C9	1.351 (9)	C7—H7	0.930
C9—C10	1.415 (9)	C8—H8	0.930
N1—H111	0.860	C9—H9	0.930
N1—H112	0.860
C1—N1—C4	104.6 (4)	C1—C2—H21	110.5
C5—N2—C6	117.3 (4)	C1—C2—H22	110.5
C5—N2—C10	121.8 (4)	C3—C2—H21	110.5
C6—N2—C10	120.8 (5)	C3—C2—H22	110.5
N1—C1—C2	103.4 (4)	H21—C2—H22	109.5
N1—C1—C5	112.4 (4)	C2—C3—H31	110.1
C2—C1—C5	113.1 (4)	C2—C3—H32	110.1
C1—C2—C3	105.5 (5)	C4—C3—H31	110.1
C2—C3—C4	106.9 (7)	C4—C3—H32	110.1
N1—C4—C3	104.4 (5)	H31—C3—H32	109.5
N2—C5—C1	114.3 (4)	N1—C4—H41	110.7
N2—C6—C7	121.7 (6)	N1—C4—H42	110.7
C6—C7—C8	118.3 (6)	C3—C4—H41	110.7
C7—C8—C9	119.7 (6)	C3—C4—H42	110.7
C8—C9—C10	121.2 (6)	H41—C4—H42	109.5
N2—C10—N3	121.3 (5)	N2—C5—H51	108.3
N2—C10—C9	118.2 (5)	N2—C5—H52	108.3
N3—C10—C9	120.5 (5)	C1—C5—H51	108.3
C1—N1—H111	110.7	C1—C5—H52	108.3
C1—N1—H112	110.7	H51—C5—H52	109.5
C4—N1—H111	110.7	N2—C6—H6	119.2
C4—N1—H112	110.7	C7—C6—H6	119.2
H111—N1—H112	109.5	C6—C7—H7	120.8
C10—N3—H301	120.0	C8—C7—H7	120.8
C10—N3—H302	120.0	C7—C8—H8	120.1
H301—N3—H302	120.0	C9—C8—H8	120.1
N1—C1—H5	109.3	C8—C9—H9	119.4
C2—C1—H5	109.3	C10—C9—H9	119.4
C5—C1—H5	109.3
C1—N1—C4—C3	−38.1 (6)	N1—C1—C2—C3	−23.1 (6)
C4—N1—C1—C2	37.7 (6)	N1—C1—C5—N2	58.8 (6)
C4—N1—C1—C5	159.9 (5)	C2—C1—C5—N2	175.4 (4)
C5—N2—C6—C7	−179.0 (6)	C5—C1—C2—C3	−144.9 (5)
C6—N2—C5—C1	−95.2 (6)	C1—C2—C3—C4	0.0 (6)
C5—N2—C10—N3	−2.4 (8)	C2—C3—C4—N1	23.0 (7)
C5—N2—C10—C9	178.4 (5)	N2—C6—C7—C8	0.3 (8)
C10—N2—C5—C1	85.4 (6)	C6—C7—C8—C9	−0.4 (9)
C6—N2—C10—N3	178.2 (5)	C7—C8—C9—C10	−0.1 (8)
C6—N2—C10—C9	−0.9 (8)	C8—C9—C10—N2	0.8 (9)
C10—N2—C6—C7	0.4 (8)	C8—C9—C10—N3	−178.4 (6)