4-Cyano-1-methyl-pyridinium bromide.

In the crystal of the title mol-ecular salt, C(7)H(7)N(2) (+)·Br(-), the cations form inversion dimers via weak pairwise C-H⋯N hydrogen bonds; their mean planes are separated by 0.292 (6) Å. Weak C-H⋯Br inter-actions involving all of the remaining H atoms tie the cations and anions together into sets of inter-penetrating sheets. The title compound is isostructural with its iodide analogue.

Related literature

For the structure of the 4-cyano-1-methyl­pyridinium iodide salt, see: Kammer et al. (2012 ▶). For the structure of 3-cyano-1-methyl­pyridinium bromide, see: Mague et al. (2005 ▶). For the structure of 3-cyano-1-methyl­pyridinium chloride, see: Koplitz et al. (2003 ▶.

Experimental

Crystal data

C7H7N2 +·Br−

M = 199.06

Monoclinic,

a = 4.5447 (16) Å

b = 11.285 (4) Å

c = 15.551 (6) Å

β = 96.455 (5)°

V = 792.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 5.11 mm−1

T = 100 K

0.26 × 0.22 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: numerical (SADABS; Bruker, 2009 ▶) T min = 0.351, T max = 0.563

12985 measured reflections

2050 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.07

2050 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.72 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030449/hb6887sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030449/hb6887Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030449/hb6887Isup3.cml

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

C7H7N2+·Br−	F(000) = 392
Mr = 199.06	Dx = 1.668 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9556 reflections
a = 4.5447 (16) Å	θ = 2.6–29.1°
b = 11.285 (4) Å	µ = 5.11 mm−1
c = 15.551 (6) Å	T = 100 K
β = 96.455 (5)°	Slab, yellow
V = 792.5 (5) Å3	0.26 × 0.22 × 0.13 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2050 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 29.1°, θmin = 2.2°
Absorption correction: numerical (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.351, Tmax = 0.563	k = −15→15
12985 measured reflections	l = −20→20

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.039P)2 + 0.1785P] where P = (Fo2 + 2Fc2)/3
2050 reflections	(Δ/σ)max = 0.002
92 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.72 e Å−3

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5 °. in omega, colllected at phi = 0.00, 90.00 and 180.00 °. and 2 sets of 800 frames, each of width 0.45 ° in phi, collected at omega = -30.00 and 210.00 °. The scan time was 20sec/frame.

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. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms.

	x	y	z	Uiso*/Ueq
Br1	0.38940 (3)	0.377230 (14)	0.850526 (11)	0.01629 (9)
N1	−0.0140 (3)	0.65445 (13)	0.81550 (10)	0.0142 (3)
N2	0.3192 (4)	0.93928 (14)	1.08002 (11)	0.0246 (4)
C1	−0.1282 (4)	0.58354 (16)	0.73879 (11)	0.0181 (3)
H1A	0.0322	0.5352	0.7202	0.027*
H1B	−0.2044	0.6368	0.6917	0.027*
H1C	−0.2881	0.5318	0.7537	0.027*
C2	0.1619 (4)	0.74794 (15)	0.80376 (11)	0.0166 (3)
H2	0.2143	0.7655	0.7477	0.020*
C3	0.2658 (4)	0.81810 (15)	0.87348 (12)	0.0180 (3)
H3	0.3935	0.8832	0.8663	0.022*
C4	0.1801 (4)	0.79167 (15)	0.95433 (11)	0.0160 (3)
C5	0.0060 (4)	0.69212 (15)	0.96585 (12)	0.0184 (3)
H5	−0.0465	0.6717	1.0214	0.022*
C6	−0.0873 (4)	0.62429 (14)	0.89416 (13)	0.0172 (4)
H6	−0.2043	0.5557	0.9003	0.021*
C7	0.2641 (5)	0.87129 (15)	1.02619 (14)	0.0202 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.01641 (13)	0.01499 (12)	0.01814 (14)	−0.00147 (5)	0.00490 (8)	−0.00055 (5)
N1	0.0167 (7)	0.0123 (6)	0.0134 (7)	0.0003 (5)	0.0003 (5)	−0.0007 (5)
N2	0.0304 (9)	0.0227 (8)	0.0205 (8)	−0.0056 (6)	0.0020 (7)	−0.0010 (6)
C1	0.0250 (9)	0.0148 (8)	0.0142 (8)	−0.0032 (6)	0.0000 (7)	−0.0033 (7)
C2	0.0178 (8)	0.0160 (7)	0.0161 (8)	−0.0006 (6)	0.0021 (6)	0.0031 (6)
C3	0.0193 (8)	0.0144 (7)	0.0198 (9)	−0.0036 (6)	0.0002 (6)	0.0025 (7)
C4	0.0172 (8)	0.0148 (7)	0.0156 (8)	0.0009 (6)	−0.0006 (6)	0.0004 (6)
C5	0.0207 (8)	0.0188 (8)	0.0161 (8)	−0.0014 (6)	0.0034 (6)	0.0018 (7)
C6	0.0203 (9)	0.0157 (8)	0.0156 (9)	−0.0020 (6)	0.0023 (7)	0.0018 (6)
C7	0.0209 (10)	0.0200 (9)	0.0196 (10)	−0.0022 (6)	0.0018 (8)	0.0030 (7)

N1—C6	1.347 (2)	C2—H2	0.9500
N1—C2	1.349 (2)	C3—C4	1.390 (2)
N1—C1	1.481 (2)	C3—H3	0.9500
N2—C7	1.142 (3)	C4—C5	1.397 (2)
C1—H1A	0.9800	C4—C7	1.451 (3)
C1—H1B	0.9800	C5—C6	1.379 (3)
C1—H1C	0.9800	C5—H5	0.9500
C2—C3	1.382 (2)	C6—H6	0.9500
C6—N1—C2	122.10 (15)	C2—C3—H3	120.6
C6—N1—C1	119.66 (14)	C4—C3—H3	120.6
C2—N1—C1	118.24 (14)	C3—C4—C5	120.59 (16)
N1—C1—H1A	109.5	C3—C4—C7	119.17 (16)
N1—C1—H1B	109.5	C5—C4—C7	120.19 (16)
H1A—C1—H1B	109.5	C6—C5—C4	118.02 (16)
N1—C1—H1C	109.5	C6—C5—H5	121.0
H1A—C1—H1C	109.5	C4—C5—H5	121.0
H1B—C1—H1C	109.5	N1—C6—C5	120.58 (15)
N1—C2—C3	119.84 (16)	N1—C6—H6	119.7
N1—C2—H2	120.1	C5—C6—H6	119.7
C3—C2—H2	120.1	N2—C7—C4	175.7 (2)
C2—C3—C4	118.74 (16)
C6—N1—C2—C3	−1.9 (2)	C3—C4—C5—C6	−2.6 (2)
C1—N1—C2—C3	178.19 (16)	C7—C4—C5—C6	175.03 (17)
N1—C2—C3—C4	−1.4 (2)	C2—N1—C6—C5	2.9 (3)
C2—C3—C4—C5	3.6 (2)	C1—N1—C6—C5	−177.16 (16)
C2—C3—C4—C7	−174.06 (16)	C4—C5—C6—N1	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2i	0.95	2.48	3.357 (2)	153
C5—H5···Br1ii	0.95	2.72	3.626 (2)	160
C6—H6···Br1iii	0.95	2.78	3.6779 (19)	157
C1—H1B···Br1iv	0.98	2.89	3.735 (2)	144
C1—H1C···Br1iii	0.98	2.82	3.755 (2)	160
C2—H2···Br1v	0.95	2.79	3.6253 (18)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2i	0.95	2.48	3.357 (2)	153
C5—H5⋯Br1ii	0.95	2.72	3.626 (2)	160
C6—H6⋯Br1iii	0.95	2.78	3.6779 (19)	157
C1—H1B⋯Br1iv	0.98	2.89	3.735 (2)	144
C1—H1C⋯Br1iii	0.98	2.82	3.755 (2)	160
C2—H2⋯Br1v	0.95	2.79	3.6253 (18)	147

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