1,1'-(Butane-1,4-di-yl)dipyridinium dibromide dihydrate.

The organic cation in the title compound, C(14)H(18)N(2) (2+)·2Br(-)·2H(2)O, is situated on an inversion centre. The cations, anions and water mol-ecules are linked via O-H⋯Br, C-H⋯Br and C-H⋯O hydrogen bonds, and π-π stacking inter-actions between adjacent pyridine rings, with a centroid-centroid separation of 3.8518 (17) Å.

Related literature

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

Experimental

Crystal data

C14H18N2 2+·2Br−·2H2O

M = 410.14

Monoclinic,

a = 11.0068 (13) Å

b = 7.1484 (8) Å

c = 12.0607 (13) Å

β = 111.602 (7)°

V = 882.30 (18) Å3

Z = 2

Mo Kα radiation

μ = 4.60 mm−1

T = 293 (2) K

0.21 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.393, T max = 0.478

7189 measured reflections

1723 independent reflections

1483 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 1.06

1723 reflections

92 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); 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/S1600536808000913/fb2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000913/fb2085Isup2.hkl

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

C14H18N22+·2Br–·2H2O	F000 = 412
Mr = 410.14	Dx = 1.544 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1730 reflections
a = 11.0068 (13) Å	θ = 0.5–0.6º
b = 7.1484 (8) Å	µ = 4.60 mm−1
c = 12.0607 (13) Å	T = 293 (2) K
β = 111.602 (7)º	Diamond, colourless
V = 882.30 (18) Å3	0.21 × 0.18 × 0.16 mm
Z = 2

Bruker CCD area-detector diffractometer	1723 independent reflections
Radiation source: fine-focus sealed tube	1483 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 293(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.393, Tmax = 0.478	k = −8→8
7189 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0377P)2 + 0.1891P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1723 reflections	Δρmax = 0.48 e Å−3
92 parameters	Δρmin = −0.45 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
38 constraints	Extinction coefficient: 0.073 (3)
Primary atom site location: structure-invariant direct methods

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
C1	0.6134 (3)	0.1783 (4)	0.2544 (2)	0.0512 (6)
H1	0.5228	0.1803	0.2175	0.061*
C2	0.6896 (3)	0.1660 (4)	0.1867 (2)	0.0602 (7)
H2	0.6509	0.1598	0.1040	0.072*
C3	0.8220 (3)	0.1629 (4)	0.2408 (3)	0.0627 (8)
H3	0.8741	0.1553	0.1953	0.075*
C4	0.8782 (3)	0.1710 (5)	0.3631 (3)	0.0655 (8)
H4	0.9686	0.1687	0.4012	0.079*
C5	0.7990 (3)	0.1826 (4)	0.4285 (2)	0.0515 (6)
H5	0.8359	0.1870	0.5114	0.062*
C6	0.5845 (2)	0.1926 (3)	0.4453 (2)	0.0458 (6)
H6A	0.5090	0.2711	0.4059	0.055*
H6B	0.6329	0.2462	0.5229	0.055*
C7	0.5400 (2)	−0.0023 (3)	0.46040 (19)	0.0389 (5)
H7A	0.6155	−0.0826	0.4959	0.047*
H7B	0.4875	−0.0534	0.3830	0.047*
N1	0.66903 (18)	0.1874 (3)	0.37309 (16)	0.0393 (5)
O1W	0.6333 (2)	0.5305 (3)	0.7900 (2)	0.0762 (6)
H1WA	0.6461	0.4149	0.8070	0.091*
H1WB	0.6735	0.5522	0.7437	0.091*
Br1	0.69404 (3)	0.09270 (4)	0.88751 (2)	0.05201 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0517 (15)	0.0538 (15)	0.0443 (13)	0.0009 (12)	0.0133 (12)	0.0042 (12)
C2	0.087 (2)	0.0545 (16)	0.0457 (14)	0.0055 (15)	0.0326 (15)	0.0043 (13)
C3	0.086 (2)	0.0498 (15)	0.077 (2)	−0.0030 (15)	0.0598 (19)	0.0006 (15)
C4	0.0500 (17)	0.0680 (18)	0.087 (2)	−0.0151 (15)	0.0353 (16)	−0.0133 (17)
C5	0.0428 (15)	0.0613 (16)	0.0487 (14)	−0.0095 (12)	0.0148 (12)	−0.0098 (13)
C6	0.0466 (14)	0.0484 (14)	0.0492 (13)	−0.0010 (11)	0.0253 (12)	−0.0008 (11)
C7	0.0359 (12)	0.0449 (13)	0.0359 (11)	−0.0006 (10)	0.0133 (10)	0.0009 (10)
N1	0.0417 (12)	0.0374 (11)	0.0421 (10)	−0.0042 (8)	0.0193 (9)	−0.0015 (8)
O1W	0.0797 (15)	0.0731 (13)	0.0922 (15)	0.0221 (12)	0.0509 (14)	0.0232 (13)
Br1	0.0555 (2)	0.0537 (2)	0.0485 (2)	0.00237 (12)	0.02118 (15)	0.00144 (11)

C1—N1	1.335 (3)	C5—H5	0.9300
C1—C2	1.372 (4)	C6—N1	1.490 (3)
C1—H1	0.9300	C6—C7	1.510 (3)
C2—C3	1.359 (4)	C6—H6A	0.9700
C2—H2	0.9300	C6—H6B	0.9700
C3—C4	1.375 (4)	C7—C7i	1.519 (4)
C3—H3	0.9300	C7—H7A	0.9700
C4—C5	1.377 (4)	C7—H7B	0.9700
C4—H4	0.9300	O1W—H1WA	0.8507
C5—N1	1.338 (3)	O1W—H1WB	0.8454
N1—C1—C2	120.1 (3)	N1—C6—H6A	109.6
N1—C1—H1	120.0	C7—C6—H6A	109.6
C2—C1—H1	120.0	N1—C6—H6B	109.6
C3—C2—C1	119.9 (3)	C7—C6—H6B	109.6
C3—C2—H2	120.1	H6A—C6—H6B	108.1
C1—C2—H2	120.1	C6—C7—C7i	110.2 (2)
C2—C3—C4	119.6 (2)	C6—C7—H7A	109.6
C2—C3—H3	120.2	C7i—C7—H7A	109.6
C4—C3—H3	120.2	C6—C7—H7B	109.6
C3—C4—C5	119.2 (3)	C7i—C7—H7B	109.6
C3—C4—H4	120.4	H7A—C7—H7B	108.1
C5—C4—H4	120.4	C1—N1—C5	121.2 (2)
N1—C5—C4	120.1 (3)	C1—N1—C6	119.3 (2)
N1—C5—H5	120.0	C5—N1—C6	119.4 (2)
C4—C5—H5	120.0	H1WA—O1W—H1WB	104.9
N1—C6—C7	110.37 (19)
N1—C1—C2—C3	0.1 (4)	C2—C1—N1—C6	−177.4 (2)
C1—C2—C3—C4	0.4 (5)	C4—C5—N1—C1	1.0 (4)
C2—C3—C4—C5	−0.1 (5)	C4—C5—N1—C6	177.7 (3)
C3—C4—C5—N1	−0.6 (4)	C7—C6—N1—C1	81.1 (3)
N1—C6—C7—C7i	176.9 (2)	C7—C6—N1—C5	−95.6 (3)
C2—C1—N1—C5	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···Br1	0.85	2.48	3.323 (2)	172
O1W—H1WB···Br1ii	0.85	2.53	3.375 (2)	175
C2—H2···Br1iii	0.93	2.86	3.664 (3)	145
C5—H5···O1Wiv	0.93	2.55	3.376 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯Br1	0.85	2.48	3.323 (2)	172
O1W—H1WB⋯Br1i	0.85	2.53	3.375 (2)	175
C2—H2⋯Br1ii	0.93	2.86	3.664 (3)	145
C5—H5⋯O1Wiii	0.93	2.55	3.376 (3)	148

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