2-Amino-5-methyl-pyridinium dibromo-iodate.

In the title salt, C(6)H(9)N(2) (+)·Br(2)I(-), the cation is essentially planar (r.m.s. deviation = 0.0062 Å for the non-H atoms) while the anion is almost linear with a Br-I-Br angle of 177.67 (2)°. The crystal packing shows two anions and two cations connected via N-H⋯Br and (pyridine)N-H⋯Br hydrogen-bonding inter-actions, forming centrosymmetric tetra-mers with R(4) (4)(16) ring motifs. Very weak offset aromatic π-π stacking interactions [centroid-centroid separation = 4.038 (4), slippage = 1.773 Å] also occur.

Related literature

For background to this study, see: Al-Far et al. (2012 ▶); Kochel (2006 ▶). For comparison bond lengths and angles, see: Gardberg et al. (2002 ▶); Hemamalini & Fun (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C6H9N2 +·Br2I−

M = 395.85

Triclinic,

a = 8.3648 (13) Å

b = 8.4233 (16) Å

c = 9.2321 (16) Å

α = 105.107 (16)°

β = 115.371 (16)°

γ = 98.241 (15)°

V = 542.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 10.26 mm−1

T = 293 K

0.54 × 0.39 × 0.30 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.011, T max = 0.045

4283 measured reflections

2465 independent reflections

1777 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.096

S = 1.01

2465 reflections

102 parameters

H-atom parameters constrained

Δρmax = 1.17 e Å−3

Δρmin = −0.85 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 (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/S1600536812036136/pv2581sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036136/pv2581Isup2.hkl

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

C6H9N2+·Br2I−	Z = 2
Mr = 395.85	F(000) = 364
Triclinic, P1	Dx = 2.422 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3648 (13) Å	Cell parameters from 1406 reflections
b = 8.4233 (16) Å	θ = 3.2–30.0°
c = 9.2321 (16) Å	µ = 10.26 mm−1
α = 105.107 (16)°	T = 293 K
β = 115.371 (16)°	Plate, yellow
γ = 98.241 (15)°	0.54 × 0.39 × 0.30 mm
V = 542.7 (2) Å3

Agilent Xcalibur Eos diffractometer	2465 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1777 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 16.0534 pixels mm-1	θmax = 29.1°, θmin = 3.2°
ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
Tmin = 0.011, Tmax = 0.045	l = −10→12
4283 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.035P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2465 reflections	Δρmax = 1.17 e Å−3
102 parameters	Δρmin = −0.85 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0292 (12)

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
N1	1.0416 (7)	0.3049 (7)	0.7106 (6)	0.0606 (15)
H1A	1.0387	0.3331	0.8057	0.073*
I1	0.70649 (5)	−0.04784 (5)	0.90281 (5)	0.04214 (17)
Br1	0.55742 (10)	−0.38624 (9)	0.80942 (10)	0.0661 (2)
N2	0.7745 (7)	0.3836 (7)	0.5894 (7)	0.0699 (17)
H2A	0.7751	0.4121	0.6862	0.084*
H2B	0.6882	0.3947	0.5021	0.084*
C2	0.9069 (8)	0.3223 (8)	0.5748 (8)	0.0509 (16)
Br2	0.85761 (10)	0.29148 (9)	0.98508 (9)	0.0589 (2)
C3	0.9133 (8)	0.2686 (8)	0.4207 (8)	0.0500 (15)
H3A	0.8224	0.2749	0.3211	0.060*
C4	1.0533 (8)	0.2076 (9)	0.4194 (8)	0.0551 (17)
H4A	1.0562	0.1728	0.3166	0.066*
C5	1.1936 (8)	0.1936 (8)	0.5625 (7)	0.0438 (14)
C6	1.1819 (9)	0.2455 (9)	0.7061 (9)	0.0591 (18)
H6A	1.2732	0.2406	0.8064	0.071*
C7	1.3488 (8)	0.1264 (9)	0.5598 (9)	0.0647 (19)
H7A	1.4329	0.1335	0.6734	0.097*
H7B	1.4130	0.1938	0.5211	0.097*
H7C	1.2999	0.0087	0.4830	0.097*

	U11	U22	U33	U12	U13	U23
N1	0.077 (4)	0.061 (4)	0.032 (3)	0.007 (3)	0.025 (3)	0.008 (3)
I1	0.0468 (3)	0.0479 (3)	0.0301 (2)	0.01598 (19)	0.01656 (19)	0.01427 (19)
Br1	0.0739 (5)	0.0464 (4)	0.0580 (5)	0.0088 (4)	0.0210 (4)	0.0132 (4)
N2	0.076 (4)	0.076 (5)	0.060 (4)	0.019 (3)	0.039 (3)	0.019 (4)
C2	0.052 (3)	0.050 (4)	0.046 (4)	0.002 (3)	0.023 (3)	0.018 (3)
Br2	0.0794 (5)	0.0461 (4)	0.0465 (4)	0.0117 (4)	0.0284 (4)	0.0173 (4)
C3	0.054 (4)	0.054 (4)	0.038 (4)	0.011 (3)	0.023 (3)	0.014 (3)
C4	0.062 (4)	0.058 (4)	0.041 (4)	0.008 (3)	0.026 (3)	0.014 (3)
C5	0.049 (3)	0.042 (4)	0.031 (3)	0.005 (3)	0.013 (3)	0.015 (3)
C6	0.060 (4)	0.064 (5)	0.040 (4)	0.013 (4)	0.016 (3)	0.016 (4)
C7	0.063 (4)	0.069 (5)	0.057 (5)	0.022 (4)	0.023 (4)	0.025 (4)

N1—C2	1.340 (7)	C3—H3A	0.9300
N1—C6	1.352 (8)	C4—C5	1.389 (8)
N1—H1A	0.8600	C4—H4A	0.9300
I1—Br1	2.6836 (10)	C5—C6	1.334 (8)
I1—Br2	2.7119 (10)	C5—C7	1.496 (8)
N2—C2	1.330 (7)	C6—H6A	0.9300
N2—H2A	0.8600	C7—H7A	0.9600
N2—H2B	0.8600	C7—H7B	0.9600
C2—C3	1.402 (8)	C7—H7C	0.9600
C3—C4	1.348 (8)
C2—N1—C6	123.5 (5)	C3—C4—H4A	118.0
C2—N1—H1A	118.3	C5—C4—H4A	118.0
C6—N1—H1A	118.3	C6—C5—C4	115.2 (6)
Br1—I1—Br2	177.67 (2)	C6—C5—C7	121.3 (6)
C2—N2—H2A	120.0	C4—C5—C7	123.5 (5)
C2—N2—H2B	120.0	C5—C6—N1	122.1 (6)
H2A—N2—H2B	120.0	C5—C6—H6A	118.9
N2—C2—N1	120.1 (6)	N1—C6—H6A	118.9
N2—C2—C3	123.6 (6)	C5—C7—H7A	109.5
N1—C2—C3	116.3 (6)	C5—C7—H7B	109.5
C4—C3—C2	118.9 (6)	H7A—C7—H7B	109.5
C4—C3—H3A	120.5	C5—C7—H7C	109.5
C2—C3—H3A	120.5	H7A—C7—H7C	109.5
C3—C4—C5	123.9 (6)	H7B—C7—H7C	109.5
C6—N1—C2—N2	−179.2 (6)	C3—C4—C5—C6	0.0 (10)
C6—N1—C2—C3	2.4 (9)	C3—C4—C5—C7	−179.7 (6)
N2—C2—C3—C4	−179.7 (6)	C4—C5—C6—N1	1.0 (10)
N1—C2—C3—C4	−1.4 (9)	C7—C5—C6—N1	−179.3 (6)
C2—C3—C4—C5	0.3 (10)	C2—N1—C6—C5	−2.3 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br2	0.86	2.73	3.499 (5)	150
N2—H2B···Br1i	0.86	2.70	3.545 (6)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br2	0.86	2.73	3.499 (5)	150
N2—H2B⋯Br1i	0.86	2.70	3.545 (6)	168

Symmetry code: (i) .