2,2'-Ethyl-enediisoquinolinium dibromide dihydrate.

In the title compound, C(20)H(18)N(2) (2+)·2Br(-)·2H(2)O, the complete dication is generated by a crystallographic centre of symmetry. In the crystal, O-H⋯Br, C-H⋯Br and C-H⋯O hydrogen bonds and π-π stacking [shortest centroid-centroid separation = 3.657 (2) Å] help to establish the packing.

Related literature

For background to supra­molecular chemistry related to the title compound, see: Loeb & Wisner (1998 ▶); Li (2007 ▶). For related structures, see: Li et al. (2008 ▶); Xu et al. (2007 ▶); Fan et al. (2007 ▶).

Experimental

Crystal data

C20H18N2 2+·2Br−·2H2O

M = 482.22

Triclinic,

a = 7.5203 (15) Å

b = 8.0749 (16) Å

c = 9.2059 (18) Å

α = 110.34 (3)°

β = 106.96 (3)°

γ = 97.26 (3)°

V = 484.9 (2) Å3

Z = 1

Mo Kα radiation

μ = 4.20 mm−1

T = 113 K

0.18 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.519, T max = 0.591

3994 measured reflections

2262 independent reflections

1800 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.07

2262 reflections

126 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045036/hb5199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045036/hb5199Isup2.hkl

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

C20H18N22+·2Br−·2H2O	Z = 1
Mr = 482.22	F(000) = 242
Triclinic, P1	Dx = 1.651 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5203 (15) Å	Cell parameters from 1667 reflections
b = 8.0749 (16) Å	θ = 2.5–27.9°
c = 9.2059 (18) Å	µ = 4.20 mm−1
α = 110.34 (3)°	T = 113 K
β = 106.96 (3)°	Block, light yellow
γ = 97.26 (3)°	0.18 × 0.16 × 0.14 mm
V = 484.9 (2) Å3

Rigaku Saturn CCD area-detector diffractometer	2262 independent reflections
Radiation source: rotating anode	1800 reflections with I > 2σ(I)
confocal	Rint = 0.027
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.5°
ω and φ scans	h = −8→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −8→10
Tmin = 0.519, Tmax = 0.591	l = −11→12
3994 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0391P)2] where P = (Fo2 + 2Fc2)/3
2262 reflections	(Δ/σ)max = 0.001
126 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.60 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
Br1	0.30313 (4)	0.40880 (4)	0.11468 (3)	0.02152 (11)
N1	0.4507 (3)	0.9986 (3)	0.7872 (2)	0.0144 (5)
C1	0.3923 (4)	1.1342 (4)	0.7547 (3)	0.0158 (5)
H1	0.4226	1.2506	0.8429	0.019*
C2	0.2857 (4)	1.1081 (4)	0.5912 (3)	0.0148 (5)
C3	0.2230 (4)	1.2538 (4)	0.5580 (3)	0.0211 (6)
H3	0.2509	1.3701	0.6457	0.025*
C4	0.1210 (4)	1.2239 (4)	0.3969 (4)	0.0263 (7)
H4	0.0762	1.3196	0.3727	0.032*
C5	0.0829 (4)	1.0516 (5)	0.2675 (3)	0.0260 (7)
H5	0.0148	1.0340	0.1564	0.031*
C6	0.1411 (4)	0.9094 (4)	0.2972 (3)	0.0226 (6)
H6	0.1120	0.7941	0.2078	0.027*
C7	0.2446 (4)	0.9341 (4)	0.4610 (3)	0.0159 (5)
C8	0.3097 (4)	0.7935 (4)	0.5028 (3)	0.0182 (6)
H8	0.2827	0.6753	0.4180	0.022*
C9	0.4100 (4)	0.8262 (4)	0.6625 (3)	0.0174 (6)
H9	0.4525	0.7310	0.6893	0.021*
C10	0.5660 (4)	1.0297 (4)	0.9599 (3)	0.0173 (6)
H10A	0.6328	1.1608	1.0248	0.021*
H10B	0.6643	0.9589	0.9589	0.021*
O1	0.8807 (4)	0.4163 (3)	0.1546 (3)	0.0267 (5)
H1A	0.994 (5)	0.408 (4)	0.142 (4)	0.022 (9)*
H1B	0.838 (6)	0.458 (6)	0.088 (5)	0.067 (15)*

	U11	U22	U33	U12	U13	U23
Br1	0.02605 (18)	0.02344 (16)	0.01838 (16)	0.01248 (12)	0.00851 (12)	0.00973 (12)
N1	0.0142 (11)	0.0168 (11)	0.0109 (10)	0.0027 (9)	0.0026 (9)	0.0062 (9)
C1	0.0194 (14)	0.0150 (13)	0.0136 (12)	0.0039 (11)	0.0073 (11)	0.0056 (10)
C2	0.0160 (13)	0.0176 (13)	0.0138 (12)	0.0027 (11)	0.0079 (11)	0.0083 (11)
C3	0.0245 (15)	0.0259 (15)	0.0236 (14)	0.0127 (13)	0.0146 (12)	0.0152 (13)
C4	0.0251 (16)	0.0406 (19)	0.0315 (16)	0.0139 (14)	0.0149 (14)	0.0297 (15)
C5	0.0162 (15)	0.0469 (19)	0.0175 (14)	0.0038 (14)	0.0034 (12)	0.0197 (14)
C6	0.0177 (15)	0.0316 (16)	0.0142 (13)	−0.0020 (13)	0.0041 (12)	0.0085 (12)
C7	0.0128 (13)	0.0211 (14)	0.0148 (12)	0.0016 (11)	0.0073 (11)	0.0074 (11)
C8	0.0210 (15)	0.0142 (13)	0.0145 (12)	0.0013 (11)	0.0060 (11)	0.0014 (11)
C9	0.0183 (14)	0.0150 (13)	0.0188 (13)	0.0052 (11)	0.0057 (11)	0.0073 (11)
C10	0.0177 (14)	0.0186 (14)	0.0109 (12)	0.0006 (11)	0.0004 (11)	0.0059 (11)
O1	0.0271 (13)	0.0288 (12)	0.0299 (11)	0.0089 (10)	0.0099 (10)	0.0182 (10)

N1—C1	1.324 (3)	C5—H5	0.9500
N1—C9	1.387 (3)	C6—C7	1.410 (4)
N1—C10	1.486 (3)	C6—H6	0.9500
C1—C2	1.409 (3)	C7—C8	1.417 (4)
C1—H1	0.9500	C8—C9	1.354 (4)
C2—C3	1.416 (4)	C8—H8	0.9500
C2—C7	1.418 (4)	C9—H9	0.9500
C3—C4	1.374 (4)	C10—C10i	1.521 (5)
C3—H3	0.9500	C10—H10A	0.9900
C4—C5	1.408 (4)	C10—H10B	0.9900
C4—H4	0.9500	O1—H1A	0.90 (4)
C5—C6	1.364 (4)	O1—H1B	0.81 (5)
C1—N1—C9	121.6 (2)	C5—C6—H6	120.1
C1—N1—C10	120.1 (2)	C7—C6—H6	120.1
C9—N1—C10	118.3 (2)	C6—C7—C8	123.4 (3)
N1—C1—C2	120.9 (2)	C6—C7—C2	118.5 (3)
N1—C1—H1	119.5	C8—C7—C2	118.1 (2)
C2—C1—H1	119.5	C9—C8—C7	120.6 (2)
C1—C2—C3	120.5 (2)	C9—C8—H8	119.7
C1—C2—C7	118.6 (2)	C7—C8—H8	119.7
C3—C2—C7	120.9 (2)	C8—C9—N1	120.1 (3)
C4—C3—C2	118.9 (3)	C8—C9—H9	119.9
C4—C3—H3	120.6	N1—C9—H9	119.9
C2—C3—H3	120.6	N1—C10—C10i	109.4 (3)
C3—C4—C5	120.1 (3)	N1—C10—H10A	109.8
C3—C4—H4	119.9	C10i—C10—H10A	109.8
C5—C4—H4	119.9	N1—C10—H10B	109.8
C6—C5—C4	121.8 (3)	C10i—C10—H10B	109.8
C6—C5—H5	119.1	H10A—C10—H10B	108.2
C4—C5—H5	119.1	H1A—O1—H1B	99 (4)
C5—C6—C7	119.8 (3)
C9—N1—C1—C2	0.0 (4)	C1—C2—C7—C6	−178.8 (2)
C10—N1—C1—C2	178.9 (2)	C3—C2—C7—C6	0.5 (4)
N1—C1—C2—C3	179.6 (3)	C1—C2—C7—C8	1.3 (4)
N1—C1—C2—C7	−1.0 (4)	C3—C2—C7—C8	−179.3 (3)
C1—C2—C3—C4	179.4 (3)	C6—C7—C8—C9	179.4 (3)
C7—C2—C3—C4	0.0 (4)	C2—C7—C8—C9	−0.7 (4)
C2—C3—C4—C5	−1.0 (4)	C7—C8—C9—N1	−0.2 (4)
C3—C4—C5—C6	1.4 (5)	C1—N1—C9—C8	0.6 (4)
C4—C5—C6—C7	−0.9 (4)	C10—N1—C9—C8	−178.2 (3)
C5—C6—C7—C8	179.7 (3)	C1—N1—C10—C10i	96.5 (3)
C5—C6—C7—C2	−0.1 (4)	C9—N1—C10—C10i	−84.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Br1ii	0.90 (4)	2.41 (4)	3.308 (3)	176 (3)
O1—H1B···Br1iii	0.81 (5)	2.51 (5)	3.313 (3)	178 (5)
C1—H1···Br1iv	0.95	2.84	3.593 (3)	137
C9—H9···Br1v	0.95	2.81	3.691 (3)	154
C10—H10B···Br1v	0.99	2.87	3.683 (3)	140
C3—H3···O1vi	0.95	2.57	3.396 (4)	145
C4—H4···O1vii	0.95	2.54	3.380 (4)	147
C10—H10A···O1iv	0.99	2.27	3.214 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Br1i	0.90 (4)	2.41 (4)	3.308 (3)	176 (3)
O1—H1B⋯Br1ii	0.81 (5)	2.51 (5)	3.313 (3)	178 (5)
C1—H1⋯Br1iii	0.95	2.84	3.593 (3)	137
C9—H9⋯Br1iv	0.95	2.81	3.691 (3)	154
C10—H10B⋯Br1iv	0.99	2.87	3.683 (3)	140
C3—H3⋯O1v	0.95	2.57	3.396 (4)	145
C4—H4⋯O1vi	0.95	2.54	3.380 (4)	147
C10—H10A⋯O1iii	0.99	2.27	3.214 (4)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .