Di-μ-bromido-bis-[bromido(4,4'-dimethyl-2,2'-bipyridine-κN,N')mercury(II)].

The asymmetric unit of the title compound, [Hg(2)Br(4)(C(12)H(12)N(2))(2)], contains one half-mol-ecule. The Hg(II) atom is five-coordinated in a trigonal-bipyramidal configuration by two N atoms from the chelating 4,4'-dimethyl-2,2'-bipyridine ligand, two bridging Br and one terminal Br atom, leading to a centrosymmetric dimeric mol-ecule. There is a π-π contact between the pyridine rings [centroid-to-centroid distance = 3.756 (5) Å].

Related literature

For related literature, see: Ahmadi, Kalateh, Ebadi et al. (2008 ▶); Ahmadi, Khalighi et al. (2008 ▶); Ahmadi, Kalateh, Abedi et al. (2008 ▶); Kalateh et al. (2008 ▶); Khalighi et al. (2008 ▶); Khavasi et al. (2008 ▶); Tadayon Pour et al. (2008 ▶); Yousefi, Rashidi Vahid et al. (2008 ▶); Yousefi, Tadayon Pour et al. (2008 ▶); Yousefi, Khalighi et al. (2008 ▶). For related structures, see: Craig et al. (1974 ▶); Perlepes et al. (1995 ▶).

Experimental

Crystal data

[Hg2Br4(n class="CellLine">C12H12N2)2]

M = 1089.25

Triclinic,

a = 7.3187 (15) Å

b = 9.2647 (19) Å

c = 11.345 (2) Å

α = 103.50 (3)°

β = 102.02 (3)°

γ = 107.87 (3)°

V = 678.6 (3) Å3

Z = 1

Mo Kα radiation

μ = 17.21 mm−1

T = 120 (2) K

0.45 × 0.25 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: numerical; shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005 ▶) T min = 0.008, T max = 0.180

8289 measured reflections

3632 independent reflections

3504 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.165

S = 1.07

3632 reflections

155 parameters

H-atom parameters constrained

Δρmax = 2.11 e Å−3

Δρmin = −1.85 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (n class="Chemical">Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032510/hk2544sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032510/hk2544Isup2.hkl

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

[Hg2Br4(C12H12N2)2]	Z = 1
Mr = 1089.25	F(000) = 496
Triclinic, P1	Dx = 2.665 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3187 (15) Å	Cell parameters from 1005 reflections
b = 9.2647 (19) Å	θ = 1.9–29.2°
c = 11.345 (2) Å	µ = 17.21 mm−1
α = 103.50 (3)°	T = 120 K
β = 102.02 (3)°	Block, colourless
γ = 107.87 (3)°	0.45 × 0.25 × 0.10 mm
V = 678.6 (3) Å3

Bruker SMART CCD area-detector diffractometer	3632 independent reflections
Radiation source: fine-focus sealed tube	3504 reflections with I > 2σ(I)
graphite	Rint = 0.073
φ and ω scans	θmax = 29.2°, θmin = 1.9°
Absorption correction: numerical shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005)	h = −9→10
Tmin = 0.008, Tmax = 0.180	k = −12→12
8289 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.037
3632 reflections	Δρmax = 2.11 e Å−3
155 parameters	Δρmin = −1.85 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1998), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (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
Hg1	0.53006 (3)	0.61812 (3)	−0.12572 (2)	0.0245 (2)
Br1	0.40249 (13)	0.40548 (9)	−0.34549 (8)	0.0325 (2)
Br2	0.23799 (9)	0.50603 (8)	−0.01775 (7)	0.0255 (2)
N1	0.6268 (10)	0.8331 (7)	−0.2132 (6)	0.0274 (12)
N2	0.6826 (10)	0.8668 (7)	0.0356 (7)	0.0259 (13)
C1	0.5951 (13)	0.8128 (9)	−0.3382 (7)	0.0315 (15)
H1	0.5267	0.7096	−0.3951	0.038*
C2	0.6580 (13)	0.9356 (10)	−0.3863 (7)	0.0293 (15)
H2	0.6341	0.9144	−0.4735	0.035*
C3	0.7570 (11)	1.0912 (8)	−0.3051 (7)	0.0241 (12)
C4	0.8350 (13)	1.2322 (10)	−0.3489 (8)	0.0309 (15)
H4A	0.9788	1.2815	−0.3126	0.037*
H4B	0.7755	1.3082	−0.3221	0.037*
H4C	0.8009	1.1972	−0.4399	0.037*
C5	0.7909 (11)	1.1122 (9)	−0.1742 (7)	0.0242 (13)
H5	0.8591	1.2142	−0.1154	0.029*
C6	0.7238 (10)	0.9826 (8)	−0.1321 (7)	0.0228 (12)
C7	0.7541 (9)	0.9998 (8)	0.0047 (7)	0.0224 (12)
C8	0.8549 (10)	1.1479 (8)	0.0993 (7)	0.0237 (13)
H8	0.9095	1.2390	0.0774	0.028*
C9	0.8745 (11)	1.1602 (8)	0.2269 (7)	0.0252 (13)
C10	0.9781 (15)	1.3215 (9)	0.3311 (9)	0.0369 (18)
H10A	0.9088	1.3911	0.3153	0.044*
H10B	1.1152	1.3682	0.3319	0.044*
H10C	0.9757	1.3071	0.4119	0.044*
C11	0.8008 (11)	1.0223 (8)	0.2559 (7)	0.0272 (14)
H11	0.8158	1.0256	0.3400	0.033*
C12	0.7042 (12)	0.8786 (9)	0.1588 (9)	0.0300 (14)
H12	0.6516	0.7860	0.1792	0.036*

	U11	U22	U33	U12	U13	U23
Hg1	0.0272 (3)	0.0176 (2)	0.0256 (3)	0.00731 (15)	0.00742 (15)	0.00320 (15)
Br1	0.0424 (4)	0.0215 (4)	0.0268 (4)	0.0077 (3)	0.0097 (3)	0.0018 (3)
Br2	0.0214 (4)	0.0225 (4)	0.0329 (4)	0.0098 (3)	0.0094 (3)	0.0064 (3)
N1	0.032 (3)	0.018 (3)	0.021 (3)	0.005 (2)	0.001 (2)	−0.002 (2)
N2	0.028 (3)	0.019 (2)	0.028 (3)	0.006 (2)	0.010 (2)	0.005 (2)
C1	0.043 (4)	0.023 (3)	0.019 (3)	0.006 (3)	0.005 (3)	0.002 (2)
C2	0.036 (4)	0.026 (4)	0.025 (3)	0.011 (3)	0.009 (3)	0.007 (3)
C3	0.026 (3)	0.016 (3)	0.031 (3)	0.010 (2)	0.011 (3)	0.005 (2)
C4	0.037 (4)	0.025 (3)	0.031 (4)	0.009 (3)	0.013 (3)	0.010 (3)
C5	0.029 (3)	0.021 (3)	0.023 (3)	0.010 (2)	0.010 (3)	0.005 (3)
C6	0.025 (3)	0.014 (3)	0.024 (3)	0.007 (2)	0.002 (2)	0.002 (2)
C7	0.016 (2)	0.018 (3)	0.024 (3)	0.006 (2)	−0.003 (2)	−0.001 (2)
C8	0.023 (3)	0.020 (3)	0.021 (3)	0.007 (2)	0.002 (2)	0.001 (2)
C9	0.030 (3)	0.025 (3)	0.023 (3)	0.015 (2)	0.007 (2)	0.005 (2)
C10	0.052 (5)	0.021 (3)	0.033 (4)	0.017 (3)	0.007 (3)	0.000 (3)
C11	0.028 (3)	0.024 (3)	0.025 (3)	0.012 (3)	0.005 (3)	0.001 (3)
C12	0.030 (3)	0.025 (3)	0.030 (4)	0.008 (3)	0.009 (3)	0.004 (3)

Hg1—Br2i	2.7884 (11)	C5—H5	0.9300
Br1—Hg1	2.5645 (15)	C6—N1	1.341 (8)
Br2—Hg1	2.7331 (11)	C6—C7	1.484 (10)
Br2—Hg1i	2.7884 (11)	C7—N2	1.341 (10)
N1—Hg1	2.409 (7)	C7—C8	1.393 (9)
N2—Hg1	2.346 (6)	C8—C9	1.399 (10)
C1—C2	1.370 (11)	C8—H8	0.9300
C1—N1	1.347 (10)	C9—C11	1.371 (10)
C1—H1	0.9300	C9—C10	1.520 (10)
C2—C3	1.383 (10)	C10—H10A	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C5	1.410 (11)	C10—H10C	0.9600
C3—C4	1.497 (10)	C11—C12	1.377 (10)
C4—H4A	0.9600	C11—H11	0.9300
C4—H4B	0.9600	C12—N2	1.348 (11)
C4—H4C	0.9600	C12—H12	0.9300
C5—C6	1.383 (10)
Br1—Hg1—Br2	102.48 (4)	H4A—C4—H4C	109.5
Br1—Hg1—Br2i	101.32 (4)	H4B—C4—H4C	109.5
Br2—Hg1—Br2i	87.29 (3)	C6—C5—C3	120.7 (7)
N1—Hg1—Br1	92.18 (15)	C6—C5—H5	119.9
N1—Hg1—Br2	135.51 (16)	C3—C5—H5	119.4
N1—Hg1—Br2i	130.97 (16)	N1—C6—C5	121.7 (7)
N2—Hg1—Br1	161.0 (2)	N1—C6—C7	115.9 (6)
N2—Hg1—Br2	93.17 (18)	C5—C6—C7	122.4 (6)
N2—Hg1—Br2i	89.92 (18)	N2—C7—C8	120.3 (7)
N2—Hg1—N1	69.0 (2)	N2—C7—C6	117.8 (6)
Hg1—Br2—Hg1i	92.71 (3)	C8—C7—C6	121.9 (6)
C1—N1—Hg1	124.3 (5)	C7—C8—C9	120.3 (7)
C6—N1—Hg1	118.0 (5)	C7—C8—H8	119.8
C6—N1—C1	117.6 (7)	C9—C8—H8	119.9
C7—N2—Hg1	119.1 (5)	C11—C9—C8	118.1 (7)
C12—N2—Hg1	121.6 (5)	C11—C9—C10	120.8 (7)
C12—N2—C7	119.3 (6)	C8—C9—C10	121.1 (7)
C2—C1—N1	123.7 (7)	C9—C10—H10A	109.4
C2—C1—H1	117.9	C9—C10—H10B	109.3
N1—C1—H1	118.4	H10A—C10—H10B	109.5
C1—C2—C3	120.0 (7)	C9—C10—H10C	109.7
C1—C2—H2	120.2	H10A—C10—H10C	109.5
C3—C2—H2	119.8	H10B—C10—H10C	109.5
C2—C3—C5	116.2 (7)	C9—C11—C12	119.2 (7)
C2—C3—C4	123.6 (7)	C9—C11—H11	120.9
C5—C3—C4	120.1 (6)	C12—C11—H11	119.9
C3—C4—H4A	109.7	N2—C12—C11	122.7 (7)
C3—C4—H4B	109.0	N2—C12—H12	118.6
H4A—C4—H4B	109.5	C11—C12—H12	118.7
C3—C4—H4C	109.7
Hg1i—Br2—Hg1—Br1	101.00 (4)	C3—C5—C6—N1	0.8 (11)
Hg1i—Br2—Hg1—Br2i	0.0	C3—C5—C6—C7	−179.2 (6)
Hg1i—Br2—Hg1—N1	−152.7 (2)	N1—C6—C7—N2	−0.2 (9)
Hg1i—Br2—Hg1—N2	−89.77 (18)	C5—C6—C7—N2	179.7 (7)
C1—N1—Hg1—Br1	3.2 (7)	N1—C6—C7—C8	179.1 (6)
C6—N1—Hg1—Br1	−174.7 (5)	C5—C6—C7—C8	−0.9 (10)
C1—N1—Hg1—Br2	−107.1 (6)	N2—C7—C8—C9	−2.9 (10)
C1—N1—Hg1—Br2i	110.3 (6)	C6—C7—C8—C9	177.8 (6)
C6—N1—Hg1—Br2	74.9 (6)	C7—C8—C9—C11	3.2 (10)
C6—N1—Hg1—Br2i	−67.7 (6)	C7—C8—C9—C10	−178.0 (6)
C6—N1—Hg1—N2	2.7 (5)	C8—C9—C11—C12	−2.5 (10)
C1—N1—Hg1—N2	−179.3 (7)	C10—C9—C11—C12	178.7 (7)
C7—N2—Hg1—Br1	4.9 (9)	C9—C11—C12—N2	1.6 (11)
C12—N2—Hg1—Br1	−173.5 (4)	C5—C6—N1—C1	−0.4 (11)
C7—N2—Hg1—Br2	−140.9 (5)	C7—C6—N1—C1	179.5 (6)
C7—N2—Hg1—Br2i	131.8 (5)	C5—C6—N1—Hg1	177.7 (5)
C12—N2—Hg1—Br2	40.6 (6)	C7—C6—N1—Hg1	−2.4 (8)
C12—N2—Hg1—Br2i	−46.7 (6)	C2—C1—N1—C6	0.6 (13)
C7—N2—Hg1—N1	−2.9 (5)	C2—C1—N1—Hg1	−177.3 (7)
C12—N2—Hg1—N1	178.7 (6)	C11—C12—N2—C7	−1.3 (11)
N1—C1—C2—C3	−1.2 (13)	C11—C12—N2—Hg1	177.1 (5)
C1—C2—C3—C5	1.4 (12)	C8—C7—N2—C12	1.9 (10)
C1—C2—C3—C4	178.6 (8)	C6—C7—N2—C12	−178.7 (6)
C2—C3—C5—C6	−1.2 (11)	C8—C7—N2—Hg1	−176.5 (5)
C4—C3—C5—C6	−178.5 (7)	C6—C7—N2—Hg1	2.8 (8)

Table 1

Selected bond lengths (Å)

Br1—Hg1	2.5645 (15)
Br2—Hg1	2.7331 (11)
Br2—Hg1i	2.7884 (11)
N1—Hg1	2.409 (7)
N2—Hg1	2.346 (6)

Symmetry code: (i) .