1-Allyl-2-amino-pyridin-1-ium bromide.

In the cation of the title salt, C8H11N2 (+)·Br(-), the dihedral angle between the planes of the pyridinium ring and the allyl group is 79.4 (3)°. In the crystal, N-H⋯Br and weak C-H⋯Br hydrogen bonds link the cations and anions, forming chains of alternating R 2 (1)(7) and R 4 (2)(8) rings, which run parallel to the c-axis direction. The crystal studied was an inversion twin with components in a 0.753 (12):0.247 (12) ratio.

Related literature

For related structures, see: Seethalakshmi et al. (2006a ▶,b ▶,c ▶, 2007 ▶, 2013 ▶). For the biolgical activity of alkyl-pyridinium salts, see: Sundararaman et al. (2013 ▶); Ilangovan et al. (2012 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H11N2 +·Br−

M = 215.10

Orthorhombic,

a = 7.8205 (2) Å

b = 13.3560 (3) Å

c = 8.5621 (2) Å

V = 894.32 (4) Å3

Z = 4

Mo Kα radiation

μ = 4.53 mm−1

T = 120 K

0.30 × 0.14 × 0.03 mm

Data collection

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.343, T max = 0.876

14540 measured reflections

2033 independent reflections

1960 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.053

S = 1.06

2033 reflections

110 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 945 Friedel pairs

Flack parameter: 0.247 (12)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813012452/lh5611sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012452/lh5611Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012452/lh5611Isup3.cml

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

C8H11N2+·Br−	F(000) = 432
Mr = 215.10	Dx = 1.598 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1211 reflections
a = 7.8205 (2) Å	θ = 2.9–27.5°
b = 13.3560 (3) Å	µ = 4.53 mm−1
c = 8.5621 (2) Å	T = 120 K
V = 894.32 (4) Å3	Plate, colourless
Z = 4	0.30 × 0.14 × 0.03 mm

Bruker–Nonius 95mm CCD camera on κ-goniostat diffractometer	2033 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1960 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −17→17
Tmin = 0.343, Tmax = 0.876	l = −10→11
14540 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.023	w = 1/[σ2(Fo2) + (0.0198P)2 + 0.704P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.053	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.43 e Å−3
2033 reflections	Δρmin = −0.35 e Å−3
110 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraints	Extinction coefficient: 0.0051 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 945 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.247 (12)

Experimental. The minimum and maximum absorption values stated above are those calculated in SHELXL97 from the given crystal dimensions. The ratio of minimum to maximum apparent transmission was determined experimentally as 0.611792.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.03564 (3)	0.120651 (14)	0.72785 (7)	0.01951 (9)
C1	0.2522 (4)	0.6591 (2)	0.6626 (3)	0.0171 (6)
C2	0.2481 (4)	0.75344 (18)	0.5884 (3)	0.0223 (5)
H2	0.2826	0.7598	0.4825	0.027*
C3	0.1942 (4)	0.8354 (2)	0.6696 (4)	0.0238 (6)
H3	0.1909	0.8989	0.6198	0.029*
C4	0.1434 (4)	0.8267 (2)	0.8268 (4)	0.0227 (6)
H4	0.1071	0.8837	0.8841	0.027*
C5	0.1474 (4)	0.7353 (2)	0.8941 (3)	0.0210 (5)
H5	0.1121	0.7285	0.9997	0.025*
C6	0.1943 (3)	0.55284 (19)	0.8940 (3)	0.0195 (5)
H6A	0.1970	0.5632	1.0085	0.023*
H6B	0.2962	0.5131	0.8647	0.023*
C7	0.0363 (3)	0.4961 (2)	0.8511 (3)	0.0221 (6)
H7	−0.0714	0.5267	0.8704	0.026*
C8	0.0379 (4)	0.4061 (2)	0.7883 (4)	0.0264 (6)
H8A	0.1437	0.3737	0.7678	0.032*
H8B	−0.0666	0.3736	0.7635	0.032*
N1	0.2010 (3)	0.65157 (19)	0.8142 (3)	0.0174 (5)
N2	0.3083 (3)	0.57779 (17)	0.5869 (2)	0.0208 (5)
H2A	0.339 (5)	0.524 (2)	0.630 (4)	0.049 (11)*
H2B	0.341 (5)	0.588 (3)	0.494 (3)	0.040 (10)*

	U11	U22	U33	U12	U13	U23
Br1	0.02238 (13)	0.02017 (12)	0.01599 (12)	−0.00267 (8)	−0.00157 (17)	0.00066 (16)
C1	0.0158 (12)	0.0185 (14)	0.0168 (12)	−0.0021 (11)	−0.0001 (10)	−0.0016 (10)
C2	0.0245 (13)	0.0228 (14)	0.0196 (13)	−0.0015 (11)	0.0013 (11)	0.0045 (10)
C3	0.0259 (15)	0.0163 (13)	0.0293 (15)	0.0019 (12)	−0.0013 (11)	0.0036 (10)
C4	0.0223 (14)	0.0220 (14)	0.0238 (15)	0.0013 (11)	0.0000 (11)	−0.0053 (11)
C5	0.0225 (14)	0.0230 (14)	0.0176 (12)	0.0010 (11)	−0.0009 (11)	−0.0037 (10)
C6	0.0255 (13)	0.0198 (12)	0.0131 (11)	0.0014 (10)	0.0020 (10)	0.0024 (9)
C7	0.0196 (13)	0.0238 (14)	0.0228 (14)	−0.0012 (10)	0.0014 (10)	0.0097 (11)
C8	0.0240 (14)	0.0286 (14)	0.0265 (13)	−0.0040 (11)	−0.0018 (10)	0.0051 (12)
N1	0.0211 (12)	0.0169 (11)	0.0141 (11)	−0.0002 (10)	0.0004 (10)	−0.0004 (9)
N2	0.0265 (12)	0.0215 (12)	0.0144 (11)	0.0023 (9)	0.0006 (9)	0.0014 (9)

C1—N2	1.339 (4)	C6—N1	1.486 (3)
C1—N1	1.361 (3)	C6—C7	1.496 (4)
C1—C2	1.412 (4)	C6—H6A	0.9900
C2—C3	1.364 (4)	C6—H6B	0.9900
C2—H2	0.9500	C7—C8	1.317 (4)
C3—C4	1.408 (4)	C7—H7	0.9500
C3—H3	0.9500	C8—H8A	0.9500
C4—C5	1.350 (4)	C8—H8B	0.9500
C4—H4	0.9500	N2—H2A	0.844 (18)
C5—N1	1.376 (4)	N2—H2B	0.849 (19)
C5—H5	0.9500
N2—C1—N1	119.9 (3)	C7—C6—H6A	109.3
N2—C1—C2	120.9 (3)	N1—C6—H6B	109.3
N1—C1—C2	119.2 (3)	C7—C6—H6B	109.3
C3—C2—C1	119.6 (3)	H6A—C6—H6B	108.0
C3—C2—H2	120.2	C8—C7—C6	123.7 (3)
C1—C2—H2	120.2	C8—C7—H7	118.2
C2—C3—C4	120.5 (3)	C6—C7—H7	118.2
C2—C3—H3	119.7	C7—C8—H8A	120.0
C4—C3—H3	119.7	C7—C8—H8B	120.0
C5—C4—C3	118.4 (3)	H8A—C8—H8B	120.0
C5—C4—H4	120.8	C1—N1—C5	120.2 (3)
C3—C4—H4	120.8	C1—N1—C6	120.9 (3)
C4—C5—N1	122.0 (3)	C5—N1—C6	118.8 (2)
C4—C5—H5	119.0	C1—N2—H2A	125 (3)
N1—C5—H5	119.0	C1—N2—H2B	115 (3)
N1—C6—C7	111.5 (2)	H2A—N2—H2B	118 (4)
N1—C6—H6A	109.3
N2—C1—C2—C3	−178.4 (3)	C2—C1—N1—C5	−0.5 (4)
N1—C1—C2—C3	0.4 (4)	N2—C1—N1—C6	−4.5 (4)
C1—C2—C3—C4	0.2 (4)	C2—C1—N1—C6	176.6 (3)
C2—C3—C4—C5	−0.8 (4)	C4—C5—N1—C1	0.0 (4)
C3—C4—C5—N1	0.7 (4)	C4—C5—N1—C6	−177.2 (3)
N1—C6—C7—C8	122.7 (3)	C7—C6—N1—C1	−79.8 (3)
N2—C1—N1—C5	178.3 (3)	C7—C6—N1—C5	97.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br1i	0.84 (2)	2.61 (2)	3.412 (2)	160 (4)
N2—H2B···Br1ii	0.85 (2)	2.51 (2)	3.357 (2)	175 (3)
C6—H6A···Br1iii	0.99	2.91	3.668 (3)	134
C6—H6B···Br1i	0.99	2.84	3.810 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Br1i	0.84 (2)	2.61 (2)	3.412 (2)	160 (4)
N2—H2B⋯Br1ii	0.85 (2)	2.51 (2)	3.357 (2)	175 (3)
C6—H6A⋯Br1iii	0.99	2.91	3.668 (3)	134
C6—H6B⋯Br1i	0.99	2.84	3.810 (3)	167

Symmetry codes: (i) ; (ii) ; (iii) .