N,N'-[1,4-Phenyl-enebis(methyl-ene)]bis-(N,N-diethyl-ethanaminium) dibromide.

In the crystal structure of the title compound, C(20)H(38)N(2) (2+)·2Br(-), the centroid of the aromatic ring is located on an inversion center, so that the asymmetric unit consists of one-half mol-ecule of the dication and one bromide anion. C-H⋯Br inter-actions connect the two components into a three-dimensional network. An intra-molecular C-H⋯π inter-action is also observed.

Related literature

For the properties of dicationic ionic liquids, see: Anderson et al. (2005 ▶). For the structure of p-phenyl­enedimethanaminium dibromide, see: Zhang & Han (2010 ▶).

Experimental

Crystal data

C20H38N2 2+·2Br−

M = 466.34

Monoclinic,

a = 8.2713 (5) Å

b = 14.1440 (9) Å

c = 9.0762 (6) Å

β = 97.634 (1)°

V = 1052.41 (12) Å3

Z = 2

Mo Kα radiation

μ = 3.86 mm−1

T = 100 K

0.51 × 0.47 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.244, T max = 0.346

10066 measured reflections

2304 independent reflections

2093 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.043

S = 1.06

2304 reflections

112 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000141/is5042sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000141/is5042Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000141/is5042Isup3.cml

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

C20H38N22+·2Br−	F(000) = 484
Mr = 466.34	Dx = 1.472 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8155 reflections
a = 8.2713 (5) Å	θ = 2.7–28.3°
b = 14.1440 (9) Å	µ = 3.86 mm−1
c = 9.0762 (6) Å	T = 100 K
β = 97.634 (1)°	Block, colorless
V = 1052.41 (12) Å3	0.51 × 0.47 × 0.35 mm
Z = 2

Bruker APEXII CCD diffractometer	2304 independent reflections
Radiation source: fine-focus sealed tube	2093 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.244, Tmax = 0.346	k = −16→18
10066 measured reflections	l = −11→11

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)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.043	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.019P)2 + 0.5002P] where P = (Fo2 + 2Fc2)/3
2304 reflections	(Δ/σ)max = 0.001
112 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.23 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
N1	0.82236 (14)	0.33100 (8)	0.70235 (13)	0.0099 (2)
C1	0.72184 (18)	0.46030 (11)	0.87038 (16)	0.0176 (3)
H1A	0.8299	0.4897	0.8894	0.026*
H1B	0.6651	0.4681	0.9578	0.026*
H1C	0.6585	0.4906	0.7843	0.026*
C2	0.74049 (18)	0.35590 (10)	0.83906 (15)	0.0138 (3)
H2A	0.6308	0.3267	0.8271	0.017*
H2B	0.8045	0.3266	0.9273	0.017*
C3	1.10397 (18)	0.38839 (11)	0.80909 (16)	0.0156 (3)
H3A	1.0615	0.3870	0.9049	0.023*
H3B	1.1769	0.4428	0.8062	0.023*
H3C	1.1644	0.3300	0.7967	0.023*
C4	0.96263 (16)	0.39682 (10)	0.68396 (15)	0.0120 (3)
H4A	0.9223	0.4628	0.6796	0.014*
H4B	1.0028	0.3828	0.5883	0.014*
C5	0.97084 (18)	0.18930 (11)	0.60528 (17)	0.0166 (3)
H5A	0.8954	0.1845	0.5127	0.025*
H5B	1.0132	0.1264	0.6346	0.025*
H5C	1.0616	0.2311	0.5900	0.025*
C6	0.88154 (17)	0.22941 (10)	0.72681 (16)	0.0131 (3)
H6A	0.9550	0.2263	0.8221	0.016*
H6B	0.7862	0.1887	0.7364	0.016*
C7	0.69822 (17)	0.33096 (10)	0.56112 (15)	0.0113 (3)
H7A	0.7577	0.3197	0.4750	0.014*
H7B	0.6231	0.2770	0.5668	0.014*
C8	0.59739 (16)	0.41916 (10)	0.53110 (15)	0.0110 (3)
C9	0.43874 (17)	0.42236 (10)	0.56832 (15)	0.0124 (3)
H9	0.3958	0.3692	0.6139	0.015*
C10	0.65646 (17)	0.49722 (10)	0.46095 (15)	0.0126 (3)
H10	0.7630	0.4954	0.4329	0.015*
Br1	0.937757 (16)	0.344754 (10)	0.237945 (15)	0.01420 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0107 (5)	0.0084 (6)	0.0103 (5)	0.0003 (5)	−0.0002 (4)	0.0017 (4)
C1	0.0219 (7)	0.0177 (8)	0.0136 (7)	0.0005 (6)	0.0034 (6)	−0.0040 (6)
C2	0.0152 (7)	0.0164 (7)	0.0102 (6)	−0.0006 (6)	0.0035 (5)	−0.0001 (5)
C3	0.0136 (7)	0.0160 (8)	0.0162 (7)	−0.0026 (6)	−0.0022 (5)	0.0011 (6)
C4	0.0126 (6)	0.0107 (7)	0.0126 (6)	−0.0029 (5)	0.0009 (5)	0.0008 (5)
C5	0.0162 (7)	0.0118 (7)	0.0212 (7)	0.0033 (6)	0.0005 (6)	−0.0012 (6)
C6	0.0137 (6)	0.0089 (7)	0.0160 (7)	0.0011 (6)	−0.0007 (5)	0.0034 (6)
C7	0.0111 (6)	0.0112 (7)	0.0108 (6)	−0.0007 (5)	−0.0020 (5)	−0.0008 (5)
C8	0.0122 (6)	0.0105 (7)	0.0095 (6)	0.0009 (5)	−0.0017 (5)	−0.0005 (5)
C9	0.0132 (6)	0.0115 (7)	0.0124 (6)	−0.0013 (5)	0.0011 (5)	0.0029 (5)
C10	0.0106 (6)	0.0149 (7)	0.0121 (6)	0.0001 (5)	0.0012 (5)	0.0006 (5)
Br1	0.01526 (8)	0.01314 (8)	0.01435 (8)	0.00247 (5)	0.00246 (5)	0.00042 (5)

N1—C4	1.5140 (17)	C5—C6	1.517 (2)
N1—C6	1.5246 (18)	C5—H5A	0.9800
N1—C2	1.5314 (17)	C5—H5B	0.9800
N1—C7	1.5322 (17)	C5—H5C	0.9800
C1—C2	1.516 (2)	C6—H6A	0.9900
C1—H1A	0.9800	C6—H6B	0.9900
C1—H1B	0.9800	C7—C8	1.5052 (19)
C1—H1C	0.9800	C7—H7A	0.9900
C2—H2A	0.9900	C7—H7B	0.9900
C2—H2B	0.9900	C8—C10	1.395 (2)
C3—C4	1.5225 (19)	C8—C9	1.3986 (19)
C3—H3A	0.9800	C9—C10i	1.389 (2)
C3—H3B	0.9800	C9—H9	0.9500
C3—H3C	0.9800	C10—C9i	1.389 (2)
C4—H4A	0.9900	C10—H10	0.9500
C4—H4B	0.9900
C4—N1—C6	111.08 (10)	H4A—C4—H4B	107.8
C4—N1—C2	112.07 (11)	C6—C5—H5A	109.5
C6—N1—C2	105.47 (10)	C6—C5—H5B	109.5
C4—N1—C7	110.25 (10)	H5A—C5—H5B	109.5
C6—N1—C7	106.74 (10)	C6—C5—H5C	109.5
C2—N1—C7	111.01 (10)	H5A—C5—H5C	109.5
C2—C1—H1A	109.5	H5B—C5—H5C	109.5
C2—C1—H1B	109.5	C5—C6—N1	115.13 (12)
H1A—C1—H1B	109.5	C5—C6—H6A	108.5
C2—C1—H1C	109.5	N1—C6—H6A	108.5
H1A—C1—H1C	109.5	C5—C6—H6B	108.5
H1B—C1—H1C	109.5	N1—C6—H6B	108.5
C1—C2—N1	116.30 (12)	H6A—C6—H6B	107.5
C1—C2—H2A	108.2	C8—C7—N1	116.41 (11)
N1—C2—H2A	108.2	C8—C7—H7A	108.2
C1—C2—H2B	108.2	N1—C7—H7A	108.2
N1—C2—H2B	108.2	C8—C7—H7B	108.2
H2A—C2—H2B	107.4	N1—C7—H7B	108.2
C4—C3—H3A	109.5	H7A—C7—H7B	107.3
C4—C3—H3B	109.5	C10—C8—C9	118.77 (13)
H3A—C3—H3B	109.5	C10—C8—C7	121.29 (12)
C4—C3—H3C	109.5	C9—C8—C7	119.88 (13)
H3A—C3—H3C	109.5	C10i—C9—C8	120.44 (13)
H3B—C3—H3C	109.5	C10i—C9—H9	119.8
N1—C4—C3	113.17 (11)	C8—C9—H9	119.8
N1—C4—H4A	108.9	C9i—C10—C8	120.76 (13)
C3—C4—H4A	108.9	C9i—C10—H10	119.6
N1—C4—H4B	108.9	C8—C10—H10	119.6
C3—C4—H4B	108.9

Cg is the centroid of the aromatic ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Br1	0.99	2.80	3.7565 (14)	163.
C2—H2B···Br1ii	0.99	2.90	3.7716 (14)	148.
C6—H6B···Br1iii	0.99	2.92	3.8318 (14)	153.
C7—H7B···Br1iii	0.99	2.89	3.7832 (14)	150.
C1—H1C···Cg	0.98	2.74	3.6529 (16)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the aromatic ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Br1	0.99	2.80	3.7565 (14)	163
C2—H2B⋯Br1i	0.99	2.90	3.7716 (14)	148
C6—H6B⋯Br1ii	0.99	2.92	3.8318 (14)	153
C7—H7B⋯Br1ii	0.99	2.89	3.7832 (14)	150
C1—H1C⋯Cg	0.98	2.74	3.6529 (16)	156

Symmetry codes: (i) ; (ii) .