Bromido(2,4,6-trimethyl-phen-yl)mercury(II).

Mol-ecules of the title compound, [HgBr(C(9)H(11))], are located on a crystallographic twofold rotation axis. Due to the mol-ecular symmetry, the Hg(II) atom is linearly coordinated by the ipso-C of the mesityl group and the Br atom. In the crystal, mol-ecules lie in planes parallel to (001).

Related literature

For dimesityl-mercury, see: Hayashi et al. (2011 ▶). For the synthesis of Hg[Mes]2, see: Hübner et al. (2010 ▶).

Experimental

Crystal data

[HgBr(C9H11)]

M = 399.68

Monoclinic,

a = 10.0459 (8) Å

b = 15.3072 (13) Å

c = 8.1517 (7) Å

β = 126.912 (5)°

V = 1002.27 (14) Å3

Z = 4

Mo Kα radiation

μ = 19.28 mm−1

T = 173 K

0.21 × 0.10 × 0.03 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.107, T max = 0.595

6756 measured reflections

942 independent reflections

892 reflections with I > 2σ(I)

R int = 0.103

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.057

S = 1.05

942 reflections

55 parameters

H-atom parameters constrained

Δρmax = 1.19 e Å−3

Δρmin = −0.71 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010392/tk5065sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010392/tk5065Isup2.hkl

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

[HgBr(C9H11)]	F(000) = 720
Mr = 399.68	Dx = 2.649 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8005 reflections
a = 10.0459 (8) Å	θ = 4.1–25.9°
b = 15.3072 (13) Å	µ = 19.28 mm−1
c = 8.1517 (7) Å	T = 173 K
β = 126.912 (5)°	Needle, colourless
V = 1002.27 (14) Å3	0.21 × 0.10 × 0.03 mm
Z = 4

Stoe IPDS II two-circle diffractometer	942 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	892 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.103
ω scans	θmax = 25.6°, θmin = 4.1°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −12→12
Tmin = 0.107, Tmax = 0.595	k = −18→18
6756 measured reflections	l = −9→9

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.024P)2] where P = (Fo2 + 2Fc2)/3
942 reflections	(Δ/σ)max = 0.001
55 parameters	Δρmax = 1.19 e Å−3
0 restraints	Δρmin = −0.71 e Å−3

Experimental. ;

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	0.5000	0.600559 (17)	0.7500	0.03814 (13)
Br1	0.5000	0.44177 (5)	0.7500	0.0531 (3)
C1	0.5000	0.7347 (5)	0.7500	0.0336 (15)
C2	0.6166 (6)	0.7798 (4)	0.7414 (7)	0.0331 (10)
C3	0.6142 (7)	0.8712 (4)	0.7429 (8)	0.0375 (12)
H3	0.6940	0.9024	0.7389	0.045*
C4	0.5000	0.9178 (5)	0.7500	0.0369 (18)
C5	0.7411 (7)	0.7320 (4)	0.7278 (9)	0.0422 (13)
H5A	0.7982	0.6875	0.8359	0.063*
H5B	0.8229	0.7736	0.7453	0.063*
H5C	0.6831	0.7037	0.5933	0.063*
C6	0.5000	1.0155 (5)	0.7500	0.048 (2)
H6A	0.6116	1.0368	0.8599	0.073*	0.50
H6B	0.4202	1.0368	0.7726	0.073*	0.50
H6C	0.4682	1.0368	0.6175	0.073*	0.50

	U11	U22	U33	U12	U13	U23
Hg1	0.03770 (18)	0.02853 (18)	0.0464 (2)	0.000	0.02430 (15)	0.000
Br1	0.0503 (5)	0.0291 (5)	0.0834 (7)	0.000	0.0419 (5)	0.000
C1	0.038 (4)	0.029 (3)	0.032 (4)	0.000	0.020 (3)	0.000
C2	0.030 (2)	0.038 (3)	0.026 (2)	−0.001 (2)	0.014 (2)	−0.003 (2)
C3	0.037 (3)	0.038 (3)	0.034 (3)	−0.007 (2)	0.019 (2)	−0.004 (2)
C4	0.043 (4)	0.021 (3)	0.032 (4)	0.000	0.014 (3)	0.000
C5	0.038 (3)	0.045 (3)	0.044 (3)	−0.003 (2)	0.025 (3)	−0.001 (2)
C6	0.060 (6)	0.033 (4)	0.045 (5)	0.000	0.028 (4)	0.000

Hg1—C1	2.053 (7)	C4—C3i	1.381 (7)
Hg1—Br1	2.4307 (8)	C4—C6	1.495 (10)
C1—C2i	1.397 (6)	C5—H5A	0.9800
C1—C2	1.397 (6)	C5—H5B	0.9800
C2—C3	1.400 (8)	C5—H5C	0.9800
C2—C5	1.510 (7)	C6—H6A	0.9800
C3—C4	1.381 (7)	C6—H6B	0.9800
C3—H3	0.9500	C6—H6C	0.9800
C1—Hg1—Br1	180.000 (1)	C2—C5—H5A	109.5
C2i—C1—C2	120.8 (7)	C2—C5—H5B	109.5
C2i—C1—Hg1	119.6 (3)	H5A—C5—H5B	109.5
C2—C1—Hg1	119.6 (3)	C2—C5—H5C	109.5
C1—C2—C3	118.3 (5)	H5A—C5—H5C	109.5
C1—C2—C5	121.4 (5)	H5B—C5—H5C	109.5
C3—C2—C5	120.3 (5)	C4—C6—H6A	109.5
C4—C3—C2	122.4 (5)	C4—C6—H6B	109.5
C4—C3—H3	118.8	H6A—C6—H6B	109.5
C2—C3—H3	118.8	C4—C6—H6C	109.5
C3—C4—C3i	117.8 (7)	H6A—C6—H6C	109.5
C3—C4—C6	121.1 (3)	H6B—C6—H6C	109.5
C3i—C4—C6	121.1 (3)
C2i—C1—C2—C3	0.4 (3)	C1—C2—C3—C4	−0.8 (7)
Hg1—C1—C2—C3	−179.6 (3)	C5—C2—C3—C4	178.4 (4)
C2i—C1—C2—C5	−178.8 (5)	C2—C3—C4—C3i	0.4 (4)
Hg1—C1—C2—C5	1.2 (5)	C2—C3—C4—C6	−179.6 (4)