Bis(1,3-diethyl-benzimidazolium) tetra-bromidomercurate(II).

In the title compound, (C(11)H(15)N(2))(2)[HgBr(4)], the tetra-coordinated Hg(II) center of the complex anion adopts a distorted tetra-hedral geometry [Hg-Br = 2.5755 (8)-2.623 (11) Å and Br-Hg-Br = 103.78 (19)-116.4 (3)°]. One of the Br atoms is disordered over two sites [site-occupancy factors = 0.51 (6) and 0.49 (6)]. The N-C-N angles in the cations are 110.7 (6) and 111.4 (7)°. In the crystal packing, a supra-molecular chain is formed via both weak inter-molecular C-H⋯Br hydrogen bonds and π-π aromatic ring stacking inter-actions [centroid-centroid separation = 3.803 (1) Å].

Related literature

For background to the chemistry of imidazolium compounds, see: Bourissou et al. (2000 ▶); Garrison & Youngs (2005 ▶); Hunter & Sanders (1990 ▶); Jacobsen et al. (2009 ▶); Juan & Lee (1999 ▶). For a related structure, see: Liu et al. (2003 ▶).

Experimental

Crystal data

(C11H15N2)2[HgBr4]

M = 870.73

Triclinic,

a = 8.4334 (15) Å

b = 9.9989 (16) Å

c = 18.328 (3) Å

α = 85.060 (3)°

β = 81.684 (3)°

γ = 67.250 (2)°

V = 1409.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 11.15 mm−1

T = 296 K

0.25 × 0.24 × 0.23 mm

Data collection

Bruker MART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.047, T max = 0.077

7102 measured reflections

4923 independent reflections

3711 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.081

S = 1.03

4923 reflections

294 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.57 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536809047461/zs2017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047461/zs2017Isup2.hkl

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

(C11H15N2)2[HgBr4]	Z = 2
Mr = 870.73	F(000) = 820
Triclinic, P1	Dx = 2.052 Mg m−3
Hall symbol: -P 1	Melting point = 469–471 K
a = 8.4334 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9989 (16) Å	Cell parameters from 3130 reflections
c = 18.328 (3) Å	θ = 2.5–25.5°
α = 85.060 (3)°	µ = 11.15 mm−1
β = 81.684 (3)°	T = 296 K
γ = 67.250 (2)°	Block, colourless
V = 1409.5 (4) Å3	0.25 × 0.24 × 0.23 mm

Bruker SMART APEX CCD area-detector diffractometer	4923 independent reflections
Radiation source: fine-focus sealed tube	3711 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
Tmin = 0.047, Tmax = 0.077	k = −11→11
7102 measured reflections	l = −20→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0369P)2 + 1.1891P] where P = (Fo2 + 2Fc2)/3
4923 reflections	(Δ/σ)max = 0.002
294 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.57 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	Occ. (<1)
Hg1	0.92830 (4)	0.40323 (3)	0.751796 (14)	0.05906 (11)
N1	0.6000 (7)	0.0822 (6)	0.8460 (3)	0.0596 (14)
N2	0.3689 (7)	0.2297 (6)	0.9074 (3)	0.0557 (13)
N3	0.4560 (9)	0.7998 (6)	0.6180 (3)	0.0778 (18)
N4	0.5979 (8)	0.7150 (6)	0.5126 (3)	0.0657 (15)
C1	0.5169 (9)	−0.0033 (7)	0.8841 (3)	0.0531 (16)
C2	0.3671 (9)	0.0921 (7)	0.9230 (3)	0.0557 (16)
C3	0.2517 (9)	0.0427 (9)	0.9661 (4)	0.0670 (19)
H3	0.1510	0.1063	0.9917	0.080*
C4	0.2912 (12)	−0.1027 (10)	0.9697 (4)	0.079 (2)
H4	0.2162	−0.1396	0.9984	0.095*
C5	0.4422 (12)	−0.1974 (9)	0.9311 (4)	0.077 (2)
H5	0.4652	−0.2963	0.9352	0.092*
C6	0.5578 (10)	−0.1508 (7)	0.8874 (4)	0.0655 (19)
H6	0.6579	−0.2149	0.8616	0.079*
C7	0.5054 (10)	0.2196 (7)	0.8613 (4)	0.0616 (18)
H7	0.5329	0.2980	0.8418	0.074*
C8	0.7646 (12)	0.0302 (9)	0.7957 (4)	0.088 (3)
H8A	0.7680	0.1084	0.7612	0.106*
H8B	0.7669	−0.0485	0.7675	0.106*
C9	0.9214 (12)	−0.0215 (11)	0.8349 (6)	0.117 (3)
H9A	0.9124	0.0509	0.8682	0.175*
H9B	1.0224	−0.0386	0.7996	0.175*
H9C	0.9305	−0.1100	0.8622	0.175*
C10	0.2278 (10)	0.3638 (8)	0.9367 (4)	0.077 (2)
H10A	0.1171	0.3601	0.9309	0.093*
H10B	0.2326	0.3672	0.9890	0.093*
C11	0.2388 (12)	0.4979 (8)	0.8993 (5)	0.101 (3)
H11A	0.3416	0.5084	0.9098	0.151*
H11B	0.1389	0.5802	0.9168	0.151*
H11C	0.2432	0.4920	0.8470	0.151*
C12	0.3604 (10)	0.8877 (7)	0.5645 (4)	0.0619 (18)
C13	0.4523 (9)	0.8350 (7)	0.4965 (4)	0.0545 (16)
C14	0.3935 (11)	0.9000 (8)	0.4311 (4)	0.072 (2)
H14	0.4537	0.8644	0.3858	0.086*
C15	0.2428 (12)	1.0190 (10)	0.4362 (5)	0.087 (2)
H15	0.1996	1.0669	0.3932	0.104*
C16	0.1514 (11)	1.0707 (9)	0.5050 (6)	0.087 (3)
H16	0.0478	1.1511	0.5063	0.104*
C17	0.2093 (10)	1.0075 (8)	0.5694 (5)	0.077 (2)
H17	0.1493	1.0436	0.6147	0.092*
C18	0.4168 (17)	0.8111 (10)	0.6994 (4)	0.126 (4)
H18A	0.5189	0.8092	0.7186	0.151*
H18B	0.3254	0.9048	0.7102	0.151*
C19	0.3668 (13)	0.7051 (11)	0.7371 (5)	0.116 (3)
H19A	0.2707	0.7005	0.7165	0.174*
H19B	0.3332	0.7282	0.7882	0.174*
H19C	0.4619	0.6129	0.7327	0.174*
C20	0.7368 (11)	0.6199 (9)	0.4597 (5)	0.094 (3)
H20A	0.7525	0.6768	0.4156	0.113*
H20B	0.8445	0.5822	0.4815	0.113*
C21	0.6995 (15)	0.5009 (11)	0.4393 (6)	0.131 (4)
H21A	0.6815	0.4452	0.4828	0.197*
H21B	0.7950	0.4402	0.4066	0.197*
H21C	0.5968	0.5374	0.4149	0.197*
C28	0.5942 (12)	0.6992 (8)	0.5842 (4)	0.082 (2)
H28	0.6782	0.6263	0.6084	0.099*
Br1	0.7857 (14)	0.3331 (10)	0.6509 (7)	0.068 (2)	0.49 (6)
Br1'	0.745 (4)	0.3411 (16)	0.6681 (16)	0.096 (3)	0.51 (6)
Br2	1.23998 (10)	0.21193 (8)	0.74047 (4)	0.0769 (2)
Br3	0.77611 (10)	0.41151 (9)	0.88750 (4)	0.0735 (2)
Br4	0.92020 (11)	0.66240 (8)	0.71463 (5)	0.0789 (2)

	U11	U22	U33	U12	U13	U23
Hg1	0.06174 (18)	0.05316 (17)	0.06080 (17)	−0.01868 (13)	−0.01052 (12)	−0.00390 (12)
N1	0.075 (4)	0.053 (3)	0.053 (3)	−0.029 (3)	−0.006 (3)	−0.002 (3)
N2	0.064 (4)	0.053 (3)	0.052 (3)	−0.022 (3)	−0.017 (3)	0.000 (3)
N3	0.113 (5)	0.057 (4)	0.051 (3)	−0.021 (4)	−0.004 (4)	0.000 (3)
N4	0.076 (4)	0.054 (3)	0.059 (4)	−0.022 (3)	0.005 (3)	−0.003 (3)
C1	0.070 (5)	0.059 (4)	0.040 (3)	−0.034 (4)	−0.013 (3)	0.002 (3)
C2	0.065 (4)	0.059 (4)	0.050 (4)	−0.027 (4)	−0.022 (3)	0.001 (3)
C3	0.064 (5)	0.084 (5)	0.065 (4)	−0.043 (4)	−0.008 (4)	0.007 (4)
C4	0.098 (6)	0.098 (6)	0.069 (5)	−0.067 (6)	−0.020 (5)	0.016 (5)
C5	0.108 (7)	0.070 (5)	0.071 (5)	−0.052 (5)	−0.023 (5)	0.003 (4)
C6	0.094 (6)	0.055 (4)	0.054 (4)	−0.031 (4)	−0.019 (4)	−0.003 (3)
C7	0.081 (5)	0.058 (4)	0.055 (4)	−0.037 (4)	−0.011 (4)	0.002 (3)
C8	0.123 (8)	0.065 (5)	0.067 (5)	−0.039 (5)	0.033 (5)	−0.009 (4)
C9	0.072 (6)	0.111 (7)	0.147 (9)	−0.022 (6)	0.035 (6)	−0.037 (7)
C10	0.064 (5)	0.068 (5)	0.091 (5)	−0.012 (4)	−0.020 (4)	−0.002 (4)
C11	0.112 (7)	0.052 (5)	0.135 (8)	−0.027 (5)	−0.015 (6)	−0.004 (5)
C12	0.075 (5)	0.046 (4)	0.068 (5)	−0.028 (4)	−0.001 (4)	−0.007 (3)
C13	0.063 (4)	0.051 (4)	0.057 (4)	−0.032 (3)	−0.003 (3)	0.000 (3)
C14	0.094 (6)	0.074 (5)	0.060 (4)	−0.043 (5)	−0.021 (4)	0.002 (4)
C15	0.102 (7)	0.090 (6)	0.085 (6)	−0.047 (6)	−0.047 (5)	0.016 (5)
C16	0.066 (5)	0.069 (5)	0.128 (8)	−0.022 (4)	−0.023 (5)	−0.021 (5)
C17	0.074 (5)	0.071 (5)	0.081 (6)	−0.023 (4)	−0.002 (4)	−0.016 (4)
C18	0.211 (12)	0.091 (7)	0.059 (5)	−0.045 (8)	0.008 (6)	−0.011 (5)
C19	0.137 (9)	0.141 (9)	0.079 (6)	−0.075 (7)	0.040 (6)	−0.030 (6)
C20	0.093 (6)	0.092 (6)	0.085 (6)	−0.031 (5)	0.019 (5)	−0.013 (5)
C21	0.144 (10)	0.132 (9)	0.118 (8)	−0.063 (8)	0.055 (7)	−0.066 (7)
C28	0.118 (7)	0.054 (5)	0.059 (5)	−0.018 (5)	−0.004 (5)	0.002 (4)
Br1	0.083 (3)	0.054 (3)	0.073 (3)	−0.024 (3)	−0.031 (2)	−0.003 (2)
Br1'	0.135 (8)	0.088 (4)	0.097 (7)	−0.065 (4)	−0.065 (6)	0.026 (3)
Br2	0.0681 (5)	0.0800 (5)	0.0583 (4)	0.0027 (4)	−0.0134 (4)	−0.0127 (4)
Br3	0.0739 (5)	0.0840 (5)	0.0668 (4)	−0.0379 (4)	0.0083 (4)	−0.0146 (4)
Br4	0.0853 (6)	0.0524 (4)	0.0948 (6)	−0.0268 (4)	0.0065 (4)	−0.0060 (4)

Hg1—Br2	2.5755 (8)	C9—H9B	0.9600
Hg1—Br1'	2.594 (11)	C9—H9C	0.9600
Hg1—Br4	2.5994 (9)	C10—C11	1.482 (10)
Hg1—Br3	2.6211 (8)	C10—H10A	0.9700
Hg1—Br1	2.623 (11)	C10—H10B	0.9700
N1—C7	1.325 (8)	C11—H11A	0.9600
N1—C1	1.389 (8)	C11—H11B	0.9600
N1—C8	1.482 (9)	C11—H11C	0.9600
N2—C7	1.301 (8)	C12—C17	1.368 (10)
N2—C2	1.386 (8)	C12—C13	1.396 (9)
N2—C10	1.485 (8)	C13—C14	1.376 (9)
N3—C28	1.322 (9)	C14—C15	1.362 (11)
N3—C12	1.385 (9)	C14—H14	0.9300
N3—C18	1.484 (10)	C15—C16	1.406 (12)
N4—C28	1.306 (9)	C15—H15	0.9300
N4—C13	1.392 (8)	C16—C17	1.353 (11)
N4—C20	1.478 (9)	C16—H16	0.9300
C1—C6	1.377 (9)	C17—H17	0.9300
C1—C2	1.393 (9)	C18—C19	1.384 (12)
C2—C3	1.377 (9)	C18—H18A	0.9700
C3—C4	1.358 (10)	C18—H18B	0.9700
C3—H3	0.9300	C19—H19A	0.9600
C4—C5	1.393 (11)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600
C5—C6	1.367 (10)	C20—C21	1.434 (12)
C5—H5	0.9300	C20—H20A	0.9700
C6—H6	0.9300	C20—H20B	0.9700
C7—H7	0.9300	C21—H21A	0.9600
C8—C9	1.488 (12)	C21—H21B	0.9600
C8—H8A	0.9700	C21—H21C	0.9600
C8—H8B	0.9700	C28—H28	0.9300
C9—H9A	0.9600
Br2—Hg1—Br1'	110.3 (7)	N2—C10—H10A	109.0
Br2—Hg1—Br4	111.94 (3)	C11—C10—H10B	109.0
Br1'—Hg1—Br4	108.4 (3)	N2—C10—H10B	109.0
Br2—Hg1—Br3	111.20 (3)	H10A—C10—H10B	107.8
Br1'—Hg1—Br3	107.5 (8)	C10—C11—H11A	109.5
Br4—Hg1—Br3	107.32 (3)	C10—C11—H11B	109.5
Br2—Hg1—Br1	103.78 (19)	H11A—C11—H11B	109.5
Br4—Hg1—Br1	106.1 (3)	C10—C11—H11C	109.5
Br3—Hg1—Br1	116.4 (3)	H11A—C11—H11C	109.5
C7—N1—C1	108.2 (6)	H11B—C11—H11C	109.5
C7—N1—C8	125.5 (6)	C17—C12—N3	131.7 (7)
C1—N1—C8	126.3 (6)	C17—C12—C13	121.8 (7)
C7—N2—C2	108.9 (6)	N3—C12—C13	106.4 (6)
C7—N2—C10	127.7 (6)	C14—C13—N4	132.6 (7)
C2—N2—C10	123.3 (6)	C14—C13—C12	121.4 (7)
C28—N3—C12	107.9 (6)	N4—C13—C12	106.0 (6)
C28—N3—C18	124.0 (7)	C15—C14—C13	116.7 (7)
C12—N3—C18	128.1 (7)	C15—C14—H14	121.7
C28—N4—C13	108.2 (6)	C13—C14—H14	121.7
C28—N4—C20	124.3 (7)	C14—C15—C16	121.2 (7)
C13—N4—C20	127.5 (6)	C14—C15—H15	119.4
C6—C1—N1	132.2 (7)	C16—C15—H15	119.4
C6—C1—C2	121.9 (6)	C17—C16—C15	122.2 (8)
N1—C1—C2	105.9 (6)	C17—C16—H16	118.9
C3—C2—N2	132.6 (7)	C15—C16—H16	118.9
C3—C2—C1	121.2 (6)	C16—C17—C12	116.6 (7)
N2—C2—C1	106.2 (6)	C16—C17—H17	121.7
C4—C3—C2	117.3 (7)	C12—C17—H17	121.7
C4—C3—H3	121.4	C19—C18—N3	116.4 (8)
C2—C3—H3	121.4	C19—C18—H18A	108.2
C3—C4—C5	121.1 (7)	N3—C18—H18A	108.2
C3—C4—H4	119.4	C19—C18—H18B	108.2
C5—C4—H4	119.4	N3—C18—H18B	108.2
C6—C5—C4	122.7 (7)	H18A—C18—H18B	107.3
C6—C5—H5	118.7	C18—C19—H19A	109.5
C4—C5—H5	118.7	C18—C19—H19B	109.5
C5—C6—C1	115.9 (7)	H19A—C19—H19B	109.5
C5—C6—H6	122.1	C18—C19—H19C	109.5
C1—C6—H6	122.1	H19A—C19—H19C	109.5
N2—C7—N1	110.7 (6)	H19B—C19—H19C	109.5
N2—C7—H7	124.6	C21—C20—N4	112.5 (7)
N1—C7—H7	124.6	C21—C20—H20A	109.1
N1—C8—C9	113.4 (7)	N4—C20—H20A	109.1
N1—C8—H8A	108.9	C21—C20—H20B	109.1
C9—C8—H8A	108.9	N4—C20—H20B	109.1
N1—C8—H8B	108.9	H20A—C20—H20B	107.8
C9—C8—H8B	108.9	C20—C21—H21A	109.5
H8A—C8—H8B	107.7	C20—C21—H21B	109.5
C8—C9—H9A	109.5	H21A—C21—H21B	109.5
C8—C9—H9B	109.5	C20—C21—H21C	109.5
H9A—C9—H9B	109.5	H21A—C21—H21C	109.5
C8—C9—H9C	109.5	H21B—C21—H21C	109.5
H9A—C9—H9C	109.5	N4—C28—N3	111.4 (7)
H9B—C9—H9C	109.5	N4—C28—H28	124.3
C11—C10—N2	113.0 (6)	N3—C28—H28	124.3
C11—C10—H10A	109.0
C7—N1—C1—C6	179.5 (7)	C28—N3—C12—C17	−179.0 (8)
C8—N1—C1—C6	0.5 (11)	C18—N3—C12—C17	1.1 (14)
C7—N1—C1—C2	0.0 (7)	C28—N3—C12—C13	−1.2 (8)
C8—N1—C1—C2	−179.1 (7)	C18—N3—C12—C13	178.8 (8)
C7—N2—C2—C3	−178.2 (7)	C28—N4—C13—C14	179.4 (8)
C10—N2—C2—C3	−1.6 (10)	C20—N4—C13—C14	0.0 (12)
C7—N2—C2—C1	1.6 (7)	C28—N4—C13—C12	−0.9 (8)
C10—N2—C2—C1	178.2 (6)	C20—N4—C13—C12	179.7 (7)
C6—C1—C2—C3	−0.7 (9)	C17—C12—C13—C14	−1.0 (10)
N1—C1—C2—C3	178.9 (6)	N3—C12—C13—C14	−179.0 (6)
C6—C1—C2—N2	179.4 (5)	C17—C12—C13—N4	179.3 (6)
N1—C1—C2—N2	−1.0 (6)	N3—C12—C13—N4	1.3 (7)
N2—C2—C3—C4	−179.5 (6)	N4—C13—C14—C15	−179.6 (7)
C1—C2—C3—C4	0.7 (10)	C12—C13—C14—C15	0.8 (10)
C2—C3—C4—C5	−0.2 (11)	C13—C14—C15—C16	−0.9 (11)
C3—C4—C5—C6	−0.4 (12)	C14—C15—C16—C17	1.3 (13)
C4—C5—C6—C1	0.4 (11)	C15—C16—C17—C12	−1.4 (12)
N1—C1—C6—C5	−179.3 (6)	N3—C12—C17—C16	178.7 (8)
C2—C1—C6—C5	0.2 (9)	C13—C12—C17—C16	1.3 (11)
C2—N2—C7—N1	−1.7 (7)	C28—N3—C18—C19	−71.1 (14)
C10—N2—C7—N1	−178.1 (6)	C12—N3—C18—C19	108.8 (11)
C1—N1—C7—N2	1.1 (7)	C28—N4—C20—C21	91.6 (11)
C8—N1—C7—N2	−179.8 (7)	C13—N4—C20—C21	−89.0 (10)
C7—N1—C8—C9	97.9 (9)	C13—N4—C28—N3	0.2 (9)
C1—N1—C8—C9	−83.2 (9)	C20—N4—C28—N3	179.6 (7)
C7—N2—C10—C11	9.0 (10)	C12—N3—C28—N4	0.7 (10)
C2—N2—C10—C11	−166.8 (6)	C18—N3—C28—N4	−179.4 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Br1'	0.97	2.73	3.69 (2)	175
C8—H8B···Br4i	0.97	2.86	3.755 (8)	153
C28—H28···Br1'	0.93	2.84	3.59 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Br1′	0.97	2.73	3.69 (2)	175
C8—H8B⋯Br4i	0.97	2.86	3.755 (8)	153
C28—H28⋯Br1′	0.93	2.84	3.59 (2)	139

Symmetry code: (i) .