Bis(benzyl-trimethyl-ammonium) di-μ-bromido-bis-[dibromido-mercurate(II)].

In the crystal structure of the title compound, (C(10)H(16)N)(2)[Hg(2)Br(6)], the condensed anion consists of two edge-sharing HgBr(4) tetrahedra and is situated on a centre of symmetry. The anions are linked to the cations through weak C-H⋯Br inter-actions.

Related literature

For related structures, see: Jin & Liu (2011 ▶); Nockemann & Meyer (2002 ▶).

Experimental

Crystal data

(C10H16N)2[Hg2Br6]

M = 1181.06

Triclinic,

a = 9.0542 (11) Å

b = 9.7287 (9) Å

c = 9.894 (1) Å

α = 80.78 (1)°

β = 71.02 (1)°

γ = 62.39 (1)°

V = 730.24 (13) Å3

Z = 1

Mo Kα radiation

μ = 18.72 mm−1

T = 298 K

0.26 × 0.22 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.011, T max = 0.024

6877 measured reflections

2872 independent reflections

2166 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.131

S = 1.07

2862 reflections

139 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −1.56 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055887/cv5212sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055887/cv5212Isup2.hkl

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

(C10H16N)2[Hg2Br6]	Z = 1
Mr = 1181.06	F(000) = 536
Triclinic, P1	Dx = 2.686 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0542 (11) Å	Cell parameters from 6235 reflections
b = 9.7287 (9) Å	θ = 6.4–26°
c = 9.894 (1) Å	µ = 18.72 mm−1
α = 80.78 (1)°	T = 298 K
β = 71.02 (1)°	Block, colourless
γ = 62.39 (1)°	0.26 × 0.22 × 0.20 mm
V = 730.24 (13) Å3

Rigaku Mercury2 diffractometer	2872 independent reflections
Radiation source: fine-focus sealed tube	2166 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.2°
CCD_Profile_fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.011, Tmax = 0.024	l = −12→12
6877 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0524P)2 + 4.9831P] where P = (Fo2 + 2Fc2)/3
2862 reflections	(Δ/σ)max < 0.001
139 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −1.56 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	0.58630 (9)	0.70394 (8)	0.72319 (8)	0.0764 (2)
Br2	0.21880 (9)	0.50624 (8)	0.89596 (8)	0.0674 (2)
Br3	0.30736 (8)	0.68625 (8)	0.47194 (7)	0.0655 (2)
C1	0.9659 (8)	0.6586 (7)	0.3266 (8)	0.064 (2)
H1A	0.9220	0.6131	0.4143	0.095*
H1B	1.0736	0.6560	0.3256	0.095*
H1C	0.9853	0.6010	0.2473	0.095*
C2	0.6710 (7)	0.8258 (7)	0.3234 (7)	0.062 (2)
H2A	0.6334	0.7749	0.4096	0.094*
H2B	0.6846	0.7740	0.2423	0.094*
H2C	0.5859	0.9319	0.3234	0.094*
C3	0.8111 (8)	0.9073 (7)	0.4372 (7)	0.061 (2)
H3A	0.7292	1.0135	0.4305	0.092*
H3B	0.9198	0.9029	0.4358	0.092*
H3C	0.7667	0.8621	0.5248	0.092*
C4	0.8986 (6)	0.8952 (6)	0.1764 (6)	0.0449 (16)
H4A	0.9305	0.8282	0.0987	0.054*
H4B	0.8017	0.9924	0.1643	0.054*
C5	1.0480 (6)	0.9265 (6)	0.1642 (5)	0.0413 (16)
C6	1.2150 (8)	0.8236 (6)	0.1077 (6)	0.050 (2)
H6	1.2390	0.7280	0.0772	0.059*
C7	1.3495 (8)	0.8583 (8)	0.0949 (7)	0.060 (2)
H7	1.4641	0.7856	0.0583	0.072*
C8	1.3137 (7)	1.0004 (9)	0.1363 (6)	0.065 (2)
H8	1.4047	1.0236	0.1292	0.078*
C9	1.1445 (7)	1.1097 (7)	0.1885 (7)	0.058 (2)
H9	1.1201	1.2079	0.2134	0.069*
C10	1.0142 (7)	1.0708 (7)	0.2027 (7)	0.0511 (19)
H10	0.8994	1.1431	0.2392	0.061*
Hg1	0.45270 (3)	0.53868 (3)	0.69985 (3)	0.05152 (7)
N1	0.8382 (5)	0.8208 (5)	0.3156 (5)	0.0421 (13)

	U11	U22	U33	U12	U13	U23
Br1	0.0961 (3)	0.0828 (3)	0.0710 (4)	−0.0584 (3)	−0.0195 (3)	−0.0032 (3)
Br2	0.0621 (3)	0.0625 (3)	0.0664 (4)	−0.0297 (2)	0.0040 (3)	−0.0121 (3)
Br3	0.0604 (3)	0.0597 (4)	0.0624 (3)	−0.0061 (3)	−0.0252 (3)	−0.0135 (3)
C1	0.064 (3)	0.052 (3)	0.074 (4)	−0.023 (3)	−0.029 (3)	0.011 (3)
C2	0.053 (2)	0.075 (3)	0.073 (4)	−0.037 (2)	−0.024 (3)	0.005 (3)
C3	0.068 (3)	0.073 (3)	0.049 (3)	−0.038 (2)	−0.005 (3)	−0.018 (3)
C4	0.058 (2)	0.042 (2)	0.048 (3)	−0.0279 (18)	−0.029 (2)	0.013 (2)
C5	0.041 (2)	0.049 (3)	0.031 (2)	−0.015 (2)	−0.0154 (19)	0.005 (2)
C6	0.065 (3)	0.034 (3)	0.031 (3)	−0.014 (2)	−0.004 (2)	0.001 (2)
C7	0.042 (3)	0.072 (4)	0.045 (3)	−0.013 (3)	−0.009 (3)	0.010 (3)
C8	0.046 (2)	0.119 (5)	0.041 (3)	−0.042 (3)	−0.020 (2)	0.011 (3)
C9	0.060 (3)	0.067 (3)	0.053 (3)	−0.037 (2)	−0.014 (3)	0.006 (3)
C10	0.038 (2)	0.053 (3)	0.056 (3)	−0.023 (2)	0.002 (2)	−0.008 (2)
Hg1	0.05128 (9)	0.05610 (11)	0.04991 (12)	−0.02925 (7)	−0.00626 (9)	−0.00723 (9)
N1	0.0451 (17)	0.041 (2)	0.048 (2)	−0.0216 (14)	−0.0197 (16)	−0.0010 (17)

Br1—Hg1	2.4909 (10)	C4—N1	1.509 (7)
Br2—Hg1	2.4698 (8)	C4—H4A	0.9700
Br3—Hg1i	2.6039 (8)	C4—H4B	0.9700
Br3—Hg1	2.8318 (8)	C5—C6	1.351 (7)
C1—N1	1.475 (7)	C5—C10	1.381 (9)
C1—H1A	0.9600	C6—C7	1.371 (11)
C1—H1B	0.9600	C6—H6	0.9300
C1—H1C	0.9600	C7—C8	1.366 (11)
C2—N1	1.468 (8)	C7—H7	0.9300
C2—H2A	0.9600	C8—C9	1.377 (7)
C2—H2B	0.9600	C8—H8	0.9300
C2—H2C	0.9600	C9—C10	1.359 (10)
C3—N1	1.469 (8)	C9—H9	0.9300
C3—H3A	0.9600	C10—H10	0.9300
C3—H3B	0.9600	Hg1—Br1	2.4909 (10)
C3—H3C	0.9600	Hg1—Br3i	2.6039 (8)
C4—C5	1.484 (9)
Hg1i—Br3—Hg1	91.14 (2)	C5—C6—H6	119.5
N1—C1—H1A	109.5	C7—C6—H6	119.5
N1—C1—H1B	109.5	C8—C7—C6	119.4 (5)
H1A—C1—H1B	109.5	C8—C7—H7	120.3
N1—C1—H1C	109.5	C6—C7—H7	120.3
H1A—C1—H1C	109.5	C7—C8—C9	120.8 (7)
H1B—C1—H1C	109.5	C7—C8—H8	119.6
N1—C2—H2A	109.5	C9—C8—H8	119.6
N1—C2—H2B	109.5	C10—C9—C8	118.4 (7)
H2A—C2—H2B	109.5	C10—C9—H9	120.8
N1—C2—H2C	109.5	C8—C9—H9	120.8
H2A—C2—H2C	109.5	C9—C10—C5	121.6 (5)
H2B—C2—H2C	109.5	C9—C10—H10	119.2
N1—C3—H3A	109.5	C5—C10—H10	119.2
N1—C3—H3B	109.5	Br2—Hg1—Br1	122.26 (3)
H3A—C3—H3B	109.5	Br2—Hg1—Br1	122.26 (3)
N1—C3—H3C	109.5	Br2—Hg1—Br3i	122.24 (3)
H3A—C3—H3C	109.5	Br1—Hg1—Br3i	107.18 (3)
H3B—C3—H3C	109.5	Br1—Hg1—Br3i	107.18 (3)
C5—C4—N1	115.1 (5)	Br2—Hg1—Br3	106.40 (3)
C5—C4—H4A	108.5	Br1—Hg1—Br3	102.23 (3)
N1—C4—H4A	108.5	Br1—Hg1—Br3	102.23 (3)
C5—C4—H4B	108.5	Br3i—Hg1—Br3	88.86 (2)
N1—C4—H4B	108.5	C2—N1—C3	108.1 (4)
H4A—C4—H4B	107.5	C2—N1—C1	109.7 (5)
C6—C5—C10	118.8 (6)	C3—N1—C1	108.7 (5)
C6—C5—C4	122.6 (6)	C2—N1—C4	108.5 (5)
C10—C5—C4	118.4 (4)	C3—N1—C4	110.4 (5)
C5—C6—C7	121.0 (6)	C1—N1—C4	111.4 (4)
N1—C4—C5—C6	91.4 (6)	C6—C5—C10—C9	−1.7 (9)
N1—C4—C5—C10	−93.3 (6)	C4—C5—C10—C9	−177.2 (6)
C10—C5—C6—C7	3.1 (9)	Hg1i—Br3—Hg1—Br2	−123.39 (3)
C4—C5—C6—C7	178.3 (5)	Hg1i—Br3—Hg1—Br1	107.33 (3)
C5—C6—C7—C8	−1.8 (9)	Hg1i—Br3—Hg1—Br1	107.33 (3)
C6—C7—C8—C9	−1.1 (10)	C5—C4—N1—C2	168.8 (4)
C7—C8—C9—C10	2.4 (10)	C5—C4—N1—C3	50.6 (5)
C8—C9—C10—C5	−1.0 (10)	C5—C4—N1—C1	−70.3 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···Br1	0.96	2.86	3.776 (7)	160
C2—H2B···Br2i	0.96	2.87	3.743 (7)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3C⋯Br1	0.96	2.86	3.776 (7)	160
C2—H2B⋯Br2i	0.96	2.87	3.743 (7)	151

Symmetry code: (i) .