Bis(2,6-dimethyl-pyridinium) dibromo-iodate bromide.

In the title salt, 2C(7)H(10)N(+)·IBr(2) (-)·Br(-), each of the anions, viz. [IBr(2)](-) and Br(-), lie on a twofold axis. The IBr(2) (-) anion is almost linear, with a Br-I-Br angle of 178.25 (3)°. The cation is essentially planar (r.m.s. deviation = 0.0067 Å). In the crystal, each Br(-) anion links two cations via N-H⋯Br⋯H-N hydrogen-bonding inter-actions.

Related literature

For background to this study, see: Kochel (2006 ▶). For comparison bond lengths and angles, see: Gardberg et al. (2002 ▶); Ahmadi et al. (2008 ▶).

Experimental

Crystal data

2C7H10N+·Br2I−·Br−

M = 582.92

Monoclinic,

a = 13.8627 (16) Å

b = 11.3622 (9) Å

c = 13.8957 (15) Å

β = 108.885 (13)°

V = 2070.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 7.33 mm−1

T = 293 K

0.34 × 0.28 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.578, T max = 0.733

4417 measured reflections

1834 independent reflections

1280 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.05

1834 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.58 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/S1600536812035702/pv2580sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035702/pv2580Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035702/pv2580Isup3.cml

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

2C7H10N+·Br2I−·Br−	F(000) = 1104
Mr = 582.92	Dx = 1.870 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1414 reflections
a = 13.8627 (16) Å	θ = 3.0–29.4°
b = 11.3622 (9) Å	µ = 7.33 mm−1
c = 13.8957 (15) Å	T = 293 K
β = 108.885 (13)°	Block, orange
V = 2070.9 (4) Å3	0.34 × 0.28 × 0.15 mm
Z = 4

Agilent Xcalibur Eos diffractometer	1834 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1280 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 16.0534 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −16→12
Absorption correction: analytical (CrysAlis PRO; Agilent, 2011)	k = −12→13
Tmin = 0.578, Tmax = 0.733	l = −16→16
4417 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) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0423P)2 + 1.4129P] where P = (Fo2 + 2Fc2)/3
1834 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
I1	0.5000	0.56444 (5)	0.2500	0.0633 (2)
Br1	0.31439 (6)	0.56808 (6)	0.10417 (6)	0.0846 (3)
Br2	0.0000	0.55587 (7)	0.2500	0.0665 (3)
N1	0.1116 (3)	0.3483 (4)	0.1556 (3)	0.0529 (11)
H1A	0.0824	0.4027	0.1793	0.064*
C6	0.2531 (5)	0.3799 (6)	0.3092 (5)	0.081 (2)
H6A	0.2058	0.4369	0.3186	0.122*
H6B	0.3145	0.4188	0.3090	0.122*
H6C	0.2688	0.3237	0.3637	0.122*
C1	0.2069 (5)	0.3183 (5)	0.2109 (5)	0.0614 (16)
C5	0.0574 (5)	0.2992 (5)	0.0649 (5)	0.0654 (17)
C2	0.2529 (6)	0.2305 (6)	0.1722 (6)	0.085 (2)
H2A	0.3183	0.2057	0.2091	0.101*
C7	−0.0487 (5)	0.3421 (7)	0.0149 (5)	0.093 (2)
H7A	−0.0643	0.4021	0.0563	0.140*
H7B	−0.0955	0.2778	0.0069	0.140*
H7C	−0.0544	0.3742	−0.0506	0.140*
C4	0.1058 (8)	0.2137 (6)	0.0278 (6)	0.090 (2)
H4A	0.0720	0.1780	−0.0341	0.108*
C3	0.2038 (8)	0.1805 (6)	0.0814 (7)	0.098 (3)
H3A	0.2363	0.1235	0.0550	0.117*

	U11	U22	U33	U12	U13	U23
I1	0.0866 (5)	0.0525 (4)	0.0601 (4)	0.000	0.0366 (3)	0.000
Br1	0.0928 (6)	0.0837 (5)	0.0703 (5)	0.0069 (4)	0.0166 (4)	−0.0037 (4)
Br2	0.0573 (5)	0.0564 (5)	0.0949 (7)	0.000	0.0371 (5)	0.000
N1	0.059 (3)	0.046 (3)	0.059 (3)	0.006 (2)	0.026 (2)	0.005 (2)
C6	0.065 (4)	0.083 (5)	0.082 (5)	0.005 (4)	0.005 (4)	−0.001 (4)
C1	0.058 (4)	0.056 (4)	0.074 (4)	0.010 (3)	0.028 (3)	0.023 (3)
C5	0.088 (5)	0.058 (4)	0.058 (4)	−0.014 (4)	0.034 (4)	−0.002 (3)
C2	0.098 (6)	0.068 (5)	0.107 (6)	0.035 (4)	0.061 (5)	0.032 (4)
C7	0.076 (5)	0.116 (6)	0.078 (5)	−0.017 (5)	0.012 (4)	0.001 (4)
C4	0.152 (8)	0.063 (5)	0.068 (5)	−0.018 (5)	0.054 (5)	−0.014 (4)
C3	0.151 (8)	0.066 (5)	0.101 (6)	0.031 (5)	0.076 (6)	0.011 (5)

I1—Br1	2.7117 (9)	C1—C2	1.383 (9)
I1—Br1i	2.7117 (9)	C5—C4	1.372 (9)
Br2—Br2ii	0.0000	C5—C7	1.490 (9)
Br2—Br2	0.0000	C2—C3	1.350 (10)
N1—C1	1.340 (7)	C2—H2A	0.9300
N1—C5	1.361 (7)	C7—H7A	0.9600
N1—H1A	0.8600	C7—H7B	0.9600
C6—C1	1.483 (8)	C7—H7C	0.9600
C6—H6A	0.9600	C4—C3	1.373 (10)
C6—H6B	0.9600	C4—H4A	0.9300
C6—H6C	0.9600	C3—H3A	0.9300
Br1—I1—Br1i	178.25 (3)	C4—C5—C7	125.8 (7)
Br2ii—Br2—Br2	0 (10)	C3—C2—C1	120.7 (7)
C1—N1—C5	125.0 (5)	C3—C2—H2A	119.6
C1—N1—H1A	117.5	C1—C2—H2A	119.6
C5—N1—H1A	117.5	C5—C7—H7A	109.5
C1—C6—H6A	109.5	C5—C7—H7B	109.5
C1—C6—H6B	109.5	H7A—C7—H7B	109.5
H6A—C6—H6B	109.5	C5—C7—H7C	109.5
C1—C6—H6C	109.5	H7A—C7—H7C	109.5
H6A—C6—H6C	109.5	H7B—C7—H7C	109.5
H6B—C6—H6C	109.5	C5—C4—C3	120.6 (7)
N1—C1—C2	117.0 (6)	C5—C4—H4A	119.7
N1—C1—C6	117.4 (5)	C3—C4—H4A	119.7
C2—C1—C6	125.6 (6)	C2—C3—C4	120.1 (7)
N1—C5—C4	116.6 (6)	C2—C3—H3A	119.9
N1—C5—C7	117.6 (6)	C4—C3—H3A	119.9
C5—N1—C1—C2	−0.2 (9)	C6—C1—C2—C3	−179.9 (7)
C5—N1—C1—C6	−178.7 (5)	N1—C5—C4—C3	0.4 (9)
C1—N1—C5—C4	−0.9 (9)	C7—C5—C4—C3	−179.4 (7)
C1—N1—C5—C7	178.9 (5)	C1—C2—C3—C4	−2.2 (11)
N1—C1—C2—C3	1.8 (9)	C5—C4—C3—C2	1.1 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br2	0.86	2.45	3.315 (5)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br2	0.86	2.45	3.315 (5)	179