Octane-1,8-diyldipyridinium dibromide dihydrate.

The asymmetric unit of the title compound, C(18)H(26)N(2) (2+)·2Br(-)·2H(2)O, consists of one-half of the organic cation, one Br(-) anion and one water mol-ecule. The organic cation is situated on a centre of inversion. The dihedral angle between the pyridine ring and the plane of the central linkage is 59.3 (1)°. The cations, anions and water mol-ecules are linked via O-H⋯Br, C-H⋯Br and C-H⋯O hydrogen bonds, forming a three-dimensional framework.

Related literature

For general background, see: Day et al. (2000 ▶, 2002 ▶); Freeman et al. (1981 ▶); Kim et al. (2000 ▶).

Experimental

Crystal data

C18H26N2 2+·2Br−·2H2O

M = 466.26

Orthorhombic,

a = 9.8329 (7) Å

b = 13.3000 (11) Å

c = 16.5688 (13) Å

V = 2166.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.75 mm−1

T = 273 (2) K

0.32 × 0.24 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.380, T max = 0.536 (expected range = 0.347–0.490)

21410 measured reflections

2503 independent reflections

1842 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.01

2503 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063970/ci2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063970/ci2531Isup2.hkl

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

C18H26N22+·2(Br–)·2H2O	F000 = 952
Mr = 466.26	Dx = 1.429 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 21410 reflections
a = 9.8329 (7) Å	θ = 2.5–27.6º
b = 13.3000 (11) Å	µ = 3.75 mm−1
c = 16.5688 (13) Å	T = 273 (2) K
V = 2166.8 (3) Å3	Prism, colourless
Z = 4	0.32 × 0.24 × 0.19 mm

Bruker APEXII CCD area-detector diffractometer	2503 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 273(2) K	θmax = 27.6º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −12→12
Tmin = 0.380, Tmax = 0.536	k = −17→17
21410 measured reflections	l = −15→21

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0352P)2 + 0.8723P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2503 reflections	Δρmax = 0.25 e Å−3
109 parameters	Δρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.28891 (2)	0.652327 (19)	0.328729 (15)	0.05280 (11)
N1	0.44180 (18)	0.35645 (13)	0.32104 (10)	0.0376 (4)
C1	0.3916 (3)	0.40288 (17)	0.38614 (14)	0.0507 (6)
H1	0.3246	0.4517	0.3801	0.061*
C2	0.4380 (3)	0.3791 (2)	0.46131 (16)	0.0642 (8)
H2	0.4014	0.4105	0.5065	0.077*
C3	0.5389 (3)	0.3088 (2)	0.46995 (16)	0.0660 (8)
H3	0.5725	0.2931	0.5209	0.079*
C4	0.5895 (3)	0.2622 (2)	0.40288 (15)	0.0588 (7)
H4	0.6582	0.2146	0.4077	0.071*
C5	0.5382 (2)	0.28617 (18)	0.32886 (13)	0.0475 (6)
H5	0.5707	0.2532	0.2832	0.057*
C6	0.3864 (2)	0.37965 (18)	0.23978 (13)	0.0455 (5)
H6A	0.3137	0.4285	0.2453	0.055*
H6B	0.3476	0.3189	0.2170	0.055*
C7	0.4916 (2)	0.42052 (18)	0.18213 (12)	0.0432 (5)
H7A	0.5633	0.3712	0.1749	0.052*
H7B	0.5320	0.4808	0.2048	0.052*
C8	0.4286 (2)	0.44515 (19)	0.10078 (13)	0.0444 (5)
H8A	0.3865	0.3850	0.0791	0.053*
H8B	0.3577	0.4950	0.1084	0.053*
C9	0.5310 (2)	0.48488 (17)	0.04014 (12)	0.0408 (5)
H9A	0.5766	0.5428	0.0633	0.049*
H9B	0.5992	0.4335	0.0306	0.049*
O1W	0.1270 (2)	0.6061 (2)	0.15455 (12)	0.0973 (8)
H1WA	0.0442	0.6131	0.1647	0.117*
H1WB	0.1689	0.6117	0.1965	0.117*

	U11	U22	U33	U12	U13	U23
Br1	0.04958 (16)	0.05876 (17)	0.05006 (17)	0.00012 (12)	−0.00083 (11)	0.01642 (11)
N1	0.0424 (10)	0.0428 (10)	0.0277 (9)	−0.0036 (8)	0.0058 (7)	0.0044 (7)
C1	0.0627 (14)	0.0464 (13)	0.0429 (14)	0.0058 (12)	0.0161 (12)	0.0025 (11)
C2	0.094 (2)	0.0637 (16)	0.0345 (14)	−0.0017 (16)	0.0104 (14)	−0.0069 (12)
C3	0.081 (2)	0.0830 (19)	0.0341 (14)	−0.0090 (17)	−0.0084 (14)	0.0108 (14)
C4	0.0601 (15)	0.0672 (17)	0.0492 (15)	0.0092 (13)	−0.0038 (13)	0.0141 (13)
C5	0.0528 (14)	0.0527 (14)	0.0368 (13)	0.0072 (11)	0.0061 (11)	0.0008 (11)
C6	0.0437 (12)	0.0601 (13)	0.0326 (12)	−0.0035 (11)	−0.0004 (10)	0.0098 (11)
C7	0.0447 (12)	0.0539 (13)	0.0311 (12)	−0.0047 (11)	0.0010 (10)	0.0064 (10)
C8	0.0437 (12)	0.0590 (14)	0.0305 (11)	−0.0035 (10)	−0.0010 (10)	0.0069 (10)
C9	0.0402 (11)	0.0540 (13)	0.0281 (11)	−0.0067 (10)	−0.0031 (9)	0.0036 (10)
O1W	0.0625 (12)	0.177 (3)	0.0519 (12)	0.0086 (16)	−0.0006 (10)	−0.0161 (14)

N1—C1	1.337 (3)	C6—H6A	0.97
N1—C5	1.337 (3)	C6—H6B	0.97
N1—C6	1.485 (3)	C7—C8	1.520 (3)
C1—C2	1.364 (4)	C7—H7A	0.97
C1—H1	0.93	C7—H7B	0.97
C2—C3	1.370 (4)	C8—C9	1.518 (3)
C2—H2	0.93	C8—H8A	0.97
C3—C4	1.366 (4)	C8—H8B	0.97
C3—H3	0.93	C9—C9i	1.518 (4)
C4—C5	1.364 (3)	C9—H9A	0.97
C4—H4	0.93	C9—H9B	0.97
C5—H5	0.93	O1W—H1WA	0.84
C6—C7	1.509 (3)	O1W—H1WB	0.81
C1—N1—C5	120.42 (19)	C7—C6—H6B	108.9
C1—N1—C6	120.0 (2)	H6A—C6—H6B	107.7
C5—N1—C6	119.53 (18)	C6—C7—C8	111.07 (19)
N1—C1—C2	120.4 (2)	C6—C7—H7A	109.4
N1—C1—H1	119.8	C8—C7—H7A	109.4
C2—C1—H1	119.8	C6—C7—H7B	109.4
C1—C2—C3	119.7 (2)	C8—C7—H7B	109.4
C1—C2—H2	120.1	H7A—C7—H7B	108.0
C3—C2—H2	120.1	C9—C8—C7	113.04 (18)
C4—C3—C2	119.2 (2)	C9—C8—H8A	109.0
C4—C3—H3	120.4	C7—C8—H8A	109.0
C2—C3—H3	120.4	C9—C8—H8B	109.0
C5—C4—C3	119.4 (2)	C7—C8—H8B	109.0
C5—C4—H4	120.3	H8A—C8—H8B	107.8
C3—C4—H4	120.3	C9i—C9—C8	113.9 (2)
N1—C5—C4	120.8 (2)	C9i—C9—H9A	108.8
N1—C5—H5	119.6	C8—C9—H9A	108.8
C4—C5—H5	119.6	C9i—C9—H9B	108.8
N1—C6—C7	113.42 (17)	C8—C9—H9B	108.8
N1—C6—H6A	108.9	H9A—C9—H9B	107.7
C7—C6—H6A	108.9	H1WA—O1W—H1WB	108.2
N1—C6—H6B	108.9
C5—N1—C1—C2	0.0 (3)	C3—C4—C5—N1	1.8 (4)
C6—N1—C1—C2	177.4 (2)	C1—N1—C6—C7	120.1 (2)
N1—C1—C2—C3	1.5 (4)	C5—N1—C6—C7	−62.5 (3)
C1—C2—C3—C4	−1.3 (4)	N1—C6—C7—C8	−178.7 (2)
C2—C3—C4—C5	−0.3 (4)	C6—C7—C8—C9	−179.0 (2)
C1—N1—C5—C4	−1.6 (3)	C7—C8—C9—C9i	−177.0 (2)
C6—N1—C5—C4	−179.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···Br1	0.81	2.55	3.353 (2)	173
O1W—H1WA···Br1ii	0.84	2.57	3.392 (2)	169
C1—H1···Br1	0.93	2.82	3.596 (2)	141
C2—H2···O1Wiii	0.93	2.48	3.271 (3)	143
C5—H5···Br1iv	0.93	2.67	3.588 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯Br1	0.81	2.55	3.353 (2)	173
O1W—H1WA⋯Br1i	0.84	2.57	3.392 (2)	169
C1—H1⋯Br1	0.93	2.82	3.596 (2)	141
C2—H2⋯O1Wii	0.93	2.48	3.271 (3)	143
C5—H5⋯Br1iii	0.93	2.67	3.588 (2)	168

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