2,6-Dimethyl-pyridinium bromide.

The asymmetric unit of the title salt, C(7)H(10)N(+)·Br(-), comprises two 2,6-dimethyl-pyridinium cations and two bromide anions. One cation and one anion are situated in general positions, while the other cation and the other anion lie on a crystallographic mirror plane parallel to (010). Each pair of ions inter-act via N-H⋯Br and C-H⋯Br hydrogen bonding, generating motifs depending on the cation and anion involved. Thus, the cation and the anion on the mirror plane generate infinite chains along the c axis, while the other ionic pair leads to sheets parallel to the ac plane. In the overall crystal packing, both motifs alternate along the b axis, with a single layer of the chain motif sandwiched between two double layers of the sheet motif. The sheets and chains are further connected via aryl π-π inter-actions [centroid-centroid distances = 3.690 (2) and 3.714 (2) Å], giving a three-dimensional network.

Related literature

For background on the structural importance of noncovalent inter­actions, see: Desiraju (1997 ▶); Hunter (1994 ▶); Allen et al. (1997 ▶); Dolling et al. (2001 ▶); Panunto et al. (1987 ▶); Robinson et al. (2000 ▶). For related geometric parameters, see: Allen et al. (1987 ▶); Ahmadi et al. (2008 ▶); Amani et al. (2008 ▶); Jin et al. (2000 ▶, 2003 ▶, 2006 ▶); Nuss et al. (2005 ▶); Pan et al. (2001 ▶). For related literature on ar­yl⋯aryl inter­actions, see: Gould et al. (1985 ▶); Hunter & Sanders (1990 ▶); Hunter (1994 ▶); Singh & Thornton (1990 ▶).

Experimental

Crystal data

C7H10N+·n class="Chemical">Br−

M = 188.06

Orthorhombic,

a = 15.0788 (13) Å

b = 20.432 (3) Å

c = 7.8456 (7) Å

V = 2417.2 (5) Å3

Z = 12

Mo Kα radiation

μ = 5.02 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.242, T max = 0.367

6863 measured reflections

2194 independent reflections

1708 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.03

2194 reflections

140 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97; molecular graphics: SHELXTL and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039578/lr2077sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039578/lr2077Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039578/lr2077Isup3.cml

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

C7H10N+·Br−	F(000) = 1128
Mr = 188.06	Dx = 1.550 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 1341 reflections
a = 15.0788 (13) Å	θ = 3.0–29.3°
b = 20.432 (3) Å	µ = 5.02 mm−1
c = 7.8456 (7) Å	T = 293 K
V = 2417.2 (5) Å3	Block, colourless
Z = 12	0.30 × 0.25 × 0.20 mm

Agilent Xcalibur Eos diffractometer	2194 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1708 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.4°
ω scans	h = −17→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −23→24
Tmin = 0.242, Tmax = 0.367	l = −9→7
6863 measured reflections

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) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.7328P] where P = (Fo2 + 2Fc2)/3
2194 reflections	(Δ/σ)max = 0.001
140 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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	Occ. (<1)
N1	0.0302 (2)	0.08268 (13)	0.5688 (4)	0.0385 (7)
H1A	0.0643	0.0802	0.6564	0.046*
C1	−0.0586 (3)	0.08263 (16)	0.5951 (5)	0.0397 (9)
C2	−0.1132 (3)	0.08487 (18)	0.4561 (6)	0.0477 (10)
H2B	−0.1744	0.0839	0.4697	0.057*
C3	−0.0765 (3)	0.08853 (18)	0.2958 (6)	0.0511 (11)
H3A	−0.1134	0.0908	0.2011	0.061*
C4	0.0140 (3)	0.08893 (17)	0.2736 (5)	0.0503 (10)
H4A	0.0380	0.0910	0.1646	0.060*
C5	0.0685 (3)	0.08625 (17)	0.4130 (5)	0.0419 (10)
C6	−0.0902 (3)	0.07923 (18)	0.7754 (5)	0.0519 (11)
H6A	−0.0420	0.0892	0.8510	0.078*
H6B	−0.1117	0.0360	0.7990	0.078*
H6C	−0.1372	0.1103	0.7920	0.078*
C7	0.1671 (3)	0.08641 (19)	0.4050 (6)	0.0568 (12)
H7A	0.1896	0.1233	0.4675	0.085*
H7B	0.1857	0.0894	0.2883	0.085*
H7C	0.1895	0.0467	0.4541	0.085*
N2	0.4525 (3)	0.2500	0.7490 (5)	0.0406 (10)
H2A	0.4164	0.2500	0.6640	0.049*
C8	0.4177 (4)	0.2500	0.9087 (7)	0.0403 (13)
C9	0.4755 (4)	0.2500	1.0449 (7)	0.0450 (13)
H9A	0.4542	0.2500	1.1561	0.054*
C10	0.5655 (4)	0.2500	1.0135 (7)	0.0480 (14)
H10A	0.6049	0.2500	1.1047	0.058*
C11	0.5977 (4)	0.2500	0.8509 (8)	0.0502 (15)
H11A	0.6585	0.2500	0.8319	0.060*
C12	0.5402 (3)	0.2500	0.7161 (7)	0.0397 (12)
C13	0.3189 (4)	0.2500	0.9253 (8)	0.0522 (15)
H13A	0.2969	0.2063	0.9096	0.078*	0.50
H13B	0.2937	0.2783	0.8404	0.078*	0.50
H13C	0.3026	0.2654	1.0366	0.078*	0.50
C14	0.5682 (4)	0.2500	0.5325 (7)	0.0578 (16)
H14A	0.5901	0.2926	0.5023	0.087*	0.50
H14B	0.5182	0.2393	0.4619	0.087*	0.50
H14C	0.6141	0.2181	0.5158	0.087*	0.50
Br1	0.31927 (4)	0.2500	0.43172 (8)	0.0566 (2)
Br2	0.15804 (3)	0.07357 (3)	0.89056 (6)	0.0627 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0341 (18)	0.0458 (17)	0.0357 (17)	−0.0006 (14)	−0.0011 (14)	−0.0024 (15)
C1	0.036 (2)	0.039 (2)	0.044 (2)	−0.0048 (17)	0.0076 (19)	0.0001 (17)
C2	0.030 (2)	0.057 (2)	0.057 (3)	−0.0002 (18)	0.000 (2)	−0.004 (2)
C3	0.051 (3)	0.059 (2)	0.043 (2)	0.000 (2)	−0.008 (2)	0.001 (2)
C4	0.054 (3)	0.059 (2)	0.039 (2)	0.003 (2)	0.004 (2)	−0.002 (2)
C5	0.035 (2)	0.044 (2)	0.046 (2)	−0.0027 (17)	0.0079 (19)	−0.0013 (18)
C6	0.044 (2)	0.066 (3)	0.046 (2)	−0.003 (2)	0.010 (2)	0.003 (2)
C7	0.037 (2)	0.077 (3)	0.056 (3)	−0.002 (2)	0.009 (2)	0.001 (2)
N2	0.035 (2)	0.048 (2)	0.039 (3)	0.000	0.000 (2)	0.000
C8	0.035 (3)	0.046 (3)	0.040 (3)	0.000	0.003 (2)	0.000
C9	0.051 (3)	0.047 (3)	0.038 (3)	0.000	−0.002 (3)	0.000
C10	0.042 (3)	0.054 (3)	0.048 (3)	0.000	−0.012 (3)	0.000
C11	0.032 (3)	0.063 (4)	0.055 (4)	0.000	0.001 (3)	0.000
C12	0.034 (3)	0.042 (3)	0.043 (3)	0.000	0.002 (3)	0.000
C13	0.032 (3)	0.072 (4)	0.052 (4)	0.000	0.006 (3)	0.000
C14	0.048 (4)	0.078 (4)	0.048 (4)	0.000	0.010 (3)	0.000
Br1	0.0362 (3)	0.0925 (5)	0.0410 (3)	0.000	0.0003 (3)	0.000
Br2	0.0390 (3)	0.1034 (4)	0.0456 (3)	0.0040 (2)	−0.00588 (19)	−0.0051 (2)

N1—C1	1.354 (5)	N2—C12	1.348 (6)
N1—C5	1.354 (5)	N2—C8	1.358 (6)
N1—H1A	0.8600	N2—H2A	0.8600
C1—C2	1.368 (6)	C8—C9	1.379 (7)
C1—C6	1.494 (5)	C8—C13	1.496 (7)
C2—C3	1.376 (6)	C9—C10	1.379 (8)
C2—H2B	0.9300	C9—H9A	0.9300
C3—C4	1.376 (6)	C10—C11	1.365 (8)
C3—H3A	0.9300	C10—H10A	0.9300
C4—C5	1.369 (6)	C11—C12	1.367 (7)
C4—H4A	0.9300	C11—H11A	0.9300
C5—C7	1.487 (6)	C12—C14	1.501 (7)
C6—H6A	0.9600	C13—H13A	0.9600
C6—H6B	0.9600	C13—H13B	0.9600
C6—H6C	0.9600	C13—H13C	0.9600
C7—H7A	0.9600	C14—H14A	0.9600
C7—H7B	0.9600	C14—H14B	0.9600
C7—H7C	0.9600	C14—H14C	0.9600
C1—N1—C5	124.0 (4)	C12—N2—C8	123.8 (5)
C1—N1—H1A	118.0	C12—N2—H2A	118.1
C5—N1—H1A	117.9	C8—N2—H2A	118.1
N1—C1—C2	118.3 (4)	N2—C8—C9	118.1 (5)
N1—C1—C6	117.4 (4)	N2—C8—C13	117.7 (5)
C2—C1—C6	124.4 (4)	C9—C8—C13	124.2 (5)
C1—C2—C3	119.2 (4)	C10—C9—C8	119.0 (5)
C1—C2—H2B	120.4	C10—C9—H9A	120.5
C3—C2—H2B	120.4	C8—C9—H9A	120.5
C4—C3—C2	121.0 (4)	C11—C10—C9	121.1 (5)
C4—C3—H3A	119.5	C11—C10—H10A	119.5
C2—C3—H3A	119.5	C9—C10—H10A	119.5
C5—C4—C3	119.6 (4)	C10—C11—C12	119.9 (5)
C5—C4—H4A	120.2	C10—C11—H11A	120.1
C3—C4—H4A	120.2	C12—C11—H11A	120.1
N1—C5—C4	117.8 (4)	N2—C12—C11	118.3 (5)
N1—C5—C7	117.7 (4)	N2—C12—C14	117.3 (5)
C4—C5—C7	124.5 (4)	C11—C12—C14	124.4 (5)
C1—C6—H6A	109.5	C8—C13—H13A	109.5
C1—C6—H6B	109.5	C8—C13—H13B	109.5
H6A—C6—H6B	109.5	H13A—C13—H13B	109.5
C1—C6—H6C	109.5	C8—C13—H13C	109.5
H6A—C6—H6C	109.5	H13A—C13—H13C	109.5
H6B—C6—H6C	109.5	H13B—C13—H13C	109.5
C5—C7—H7A	109.5	C12—C14—H14A	109.5
C5—C7—H7B	109.5	C12—C14—H14B	109.5
H7A—C7—H7B	109.5	H14A—C14—H14B	109.5
C5—C7—H7C	109.5	C12—C14—H14C	109.5
H7A—C7—H7C	109.5	H14A—C14—H14C	109.5
H7B—C7—H7C	109.5	H14B—C14—H14C	109.5
C5—N1—C1—C2	1.5 (5)	C12—N2—C8—C9	0.000 (2)
C5—N1—C1—C6	−179.3 (3)	C12—N2—C8—C13	180.000 (1)
N1—C1—C2—C3	−1.4 (5)	N2—C8—C9—C10	0.000 (2)
C6—C1—C2—C3	179.4 (4)	C13—C8—C9—C10	180.000 (1)
C1—C2—C3—C4	1.0 (6)	C8—C9—C10—C11	0.000 (2)
C2—C3—C4—C5	−0.6 (6)	C9—C10—C11—C12	0.000 (2)
C1—N1—C5—C4	−1.1 (5)	C8—N2—C12—C11	0.000 (1)
C1—N1—C5—C7	179.4 (3)	C8—N2—C12—C14	180.0
C3—C4—C5—N1	0.6 (5)	C10—C11—C12—N2	0.000 (1)
C3—C4—C5—C7	−180.0 (3)	C10—C11—C12—C14	180.000 (1)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br1	0.86	2.34	3.199 (5)	180
N1—H1A···Br2	0.86	2.32	3.182 (4)	179
C4—H4A···Br2i	0.93	2.83	3.722 (5)	161
C2—H2B···Br2ii	0.93	2.76	3.664 (5)	163
C9—H9A···Br1iii	0.93	2.97	3.842 (6)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Br1	0.86	2.34	3.199 (5)	180
N1—H1A⋯Br2	0.86	2.32	3.182 (4)	179
C4—H4A⋯Br2i	0.93	2.83	3.722 (5)	161
C2—H2B⋯Br2ii	0.93	2.76	3.664 (5)	163
C9—H9A⋯Br1iii	0.93	2.97	3.842 (6)	157

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