Dibromido(2,2'-dimethyl-4,4'-bi-1,3-thia-zole-κN,N')mercury(II).

The asymmetric unit of the title compound, [HgBr(2)(C(8)H(8)N(2)S(2))], contains two crystallographically independent mol-ecules. The Hg(II) atoms are four-coordinated in a distorted tetra-hedral geometry by two N atoms from a 2,2'-dimethyl-4,4'-bi-1,3-thia-zole ligand and two Br atoms. In the crystal structure, inter-molecular C-H⋯Br hydrogen bonds and π-π contacts between the thia-zole rings [centroid-centroid distances = 3.670 (3) and 3.614 (2) Å] stabilize the structure.

Related literature

For metal complexes with 2,2′-dimethyl-4,4′-bithia­zole ligands, see: Abedi & Yahyazade Bali (2010 ▶); Al-Hashemi et al. (2009 ▶, 2010 ▶); Khavasi et al. (2008 ▶); Notash et al. (2008 ▶, 2009 ▶). For related structures, see: Kalateh et al. (2008 ▶); Safari et al. (2009 ▶).

Experimental

Crystal data

[HgBr2(C8H8N2S2)]

M = 556.69

Triclinic,

a = 10.2799 (6) Å

b = 11.1595 (7) Å

c = 11.6821 (7) Å

α = 88.4456 (11)°

β = 85.3290 (11)°

γ = 77.1162 (11)°

V = 1302.02 (14) Å3

Z = 4

Mo Kα radiation

μ = 18.25 mm−1

T = 100 K

0.14 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.070, T max = 0.240

20881 measured reflections

6912 independent reflections

5865 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.062

S = 0.94

6912 reflections

275 parameters

H-atom parameters constrained

Δρmax = 1.28 e Å−3

Δρmin = −1.68 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: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810051494/hy2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051494/hy2386Isup2.hkl

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

[HgBr2(C8H8N2S2)]	Z = 4
Mr = 556.69	F(000) = 1008
Triclinic, P1	Dx = 2.840 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2799 (6) Å	Cell parameters from 2931 reflections
b = 11.1595 (7) Å	θ = 3.0–29.0°
c = 11.6821 (7) Å	µ = 18.25 mm−1
α = 88.4456 (11)°	T = 100 K
β = 85.3290 (11)°	Prism, colorless
γ = 77.1162 (11)°	0.14 × 0.12 × 0.08 mm
V = 1302.02 (14) Å3

Bruker APEXII CCD diffractometer	6912 independent reflections
Radiation source: fine-focus sealed tube	5865 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
Tmin = 0.070, Tmax = 0.240	k = −15→15
20881 measured reflections	l = −15→15

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0299P)2 + 2.0838P] where P = (Fo2 + 2Fc2)/3
6912 reflections	(Δ/σ)max = 0.002
275 parameters	Δρmax = 1.28 e Å−3
0 restraints	Δρmin = −1.68 e Å−3

	x	y	z	Uiso*/Ueq
Hg1	1.080846 (18)	0.703396 (17)	0.207265 (14)	0.01438 (5)
Br1	1.27509 (5)	0.73077 (5)	0.07429 (4)	0.01974 (10)
Br2	1.01869 (5)	0.79183 (4)	0.40562 (4)	0.01472 (9)
S1	0.96732 (13)	0.30682 (11)	0.30191 (10)	0.0162 (2)
S2	0.74266 (12)	0.71656 (11)	−0.06846 (10)	0.0167 (2)
N1	1.0123 (4)	0.5145 (4)	0.2400 (3)	0.0126 (8)
N2	0.9123 (4)	0.6940 (3)	0.0815 (3)	0.0118 (7)
C1	1.0489 (4)	0.4251 (4)	0.3135 (4)	0.0117 (8)
C2	0.8814 (5)	0.3826 (4)	0.1925 (4)	0.0160 (9)
H2A	0.8189	0.3523	0.1522	0.019*
C3	0.9157 (5)	0.4932 (4)	0.1714 (4)	0.0129 (9)
C4	0.8605 (5)	0.7689 (4)	0.0020 (4)	0.0148 (9)
C5	0.7668 (5)	0.5861 (4)	0.0144 (4)	0.0150 (9)
H5A	0.7206	0.5217	0.0097	0.018*
C6	0.8618 (5)	0.5883 (4)	0.0881 (4)	0.0131 (9)
C7	1.1512 (5)	0.4226 (5)	0.3961 (4)	0.0186 (10)
H7A	1.1390	0.5043	0.4296	0.028*
H7B	1.2407	0.3995	0.3561	0.028*
H7C	1.1418	0.3625	0.4571	0.028*
C8	0.8973 (5)	0.8888 (4)	−0.0288 (4)	0.0189 (10)
H8A	0.9945	0.8786	−0.0294	0.028*
H8B	0.8531	0.9507	0.0280	0.028*
H8C	0.8684	0.9155	−0.1050	0.028*
Hg2	0.411665 (18)	0.785100 (16)	0.717555 (15)	0.01467 (5)
Br3	0.50713 (5)	0.58257 (4)	0.80847 (4)	0.01660 (10)
Br4	0.19137 (5)	0.93379 (4)	0.74712 (4)	0.01734 (10)
S3	0.72536 (12)	1.05628 (11)	0.68030 (10)	0.0150 (2)
S4	0.59092 (12)	0.68616 (11)	0.31954 (10)	0.0161 (2)
N3	0.5664 (4)	0.9109 (4)	0.6782 (3)	0.0142 (8)
N4	0.5044 (4)	0.7580 (3)	0.5213 (3)	0.0110 (7)
C9	0.6015 (5)	0.9912 (4)	0.7442 (4)	0.0136 (9)
C10	0.7285 (5)	0.9747 (4)	0.5581 (4)	0.0154 (9)
H10A	0.7849	0.9794	0.4904	0.018*
C11	0.6378 (4)	0.9014 (4)	0.5721 (4)	0.0114 (8)
C12	0.4840 (4)	0.6864 (4)	0.4407 (4)	0.0138 (9)
C13	0.6630 (5)	0.7909 (4)	0.3806 (4)	0.0137 (9)
H13A	0.7328	0.8249	0.3443	0.016*
C14	0.6059 (4)	0.8182 (4)	0.4879 (4)	0.0100 (8)
C15	0.5358 (5)	1.0239 (5)	0.8604 (4)	0.0176 (10)
H15A	0.4717	0.9721	0.8807	0.026*
H15B	0.4885	1.1105	0.8608	0.026*
H15C	0.6036	1.0107	0.9164	0.026*
C16	0.3766 (5)	0.6164 (5)	0.4523 (4)	0.0181 (10)
H16A	0.3632	0.5912	0.5326	0.027*
H16B	0.4023	0.5434	0.4038	0.027*
H16C	0.2932	0.6685	0.4281	0.027*

	U11	U22	U33	U12	U13	U23
Hg1	0.01399 (9)	0.01808 (10)	0.01340 (8)	−0.00844 (7)	−0.00148 (6)	0.00061 (6)
Br1	0.0193 (2)	0.0236 (3)	0.0190 (2)	−0.0124 (2)	0.00513 (19)	−0.00411 (18)
Br2	0.0117 (2)	0.0184 (2)	0.0138 (2)	−0.00327 (17)	0.00036 (16)	−0.00020 (17)
S1	0.0190 (6)	0.0165 (6)	0.0161 (5)	−0.0099 (5)	−0.0037 (4)	0.0045 (4)
S2	0.0160 (6)	0.0177 (6)	0.0179 (5)	−0.0051 (5)	−0.0079 (5)	0.0019 (4)
N1	0.0086 (18)	0.015 (2)	0.0150 (18)	−0.0052 (15)	−0.0010 (15)	0.0000 (15)
N2	0.0097 (18)	0.0125 (19)	0.0134 (18)	−0.0036 (15)	0.0000 (14)	0.0017 (14)
C1	0.007 (2)	0.012 (2)	0.015 (2)	−0.0021 (16)	0.0031 (16)	−0.0011 (16)
C2	0.017 (2)	0.020 (2)	0.014 (2)	−0.011 (2)	−0.0026 (18)	0.0032 (18)
C3	0.013 (2)	0.015 (2)	0.011 (2)	−0.0035 (18)	−0.0011 (17)	0.0001 (16)
C4	0.017 (2)	0.018 (2)	0.011 (2)	−0.0052 (19)	−0.0008 (17)	−0.0031 (17)
C5	0.014 (2)	0.016 (2)	0.015 (2)	−0.0045 (18)	−0.0055 (18)	0.0006 (17)
C6	0.009 (2)	0.016 (2)	0.015 (2)	−0.0045 (18)	0.0010 (17)	−0.0052 (17)
C7	0.018 (2)	0.022 (3)	0.019 (2)	−0.008 (2)	−0.0075 (19)	0.0053 (19)
C8	0.020 (3)	0.015 (2)	0.023 (2)	−0.005 (2)	−0.004 (2)	−0.0003 (19)
Hg2	0.01185 (9)	0.01587 (9)	0.01664 (9)	−0.00476 (7)	0.00171 (7)	−0.00051 (6)
Br3	0.0161 (2)	0.0170 (2)	0.0169 (2)	−0.00399 (18)	−0.00171 (17)	0.00080 (17)
Br4	0.0137 (2)	0.0168 (2)	0.0201 (2)	−0.00250 (18)	0.00373 (18)	0.00131 (17)
S3	0.0160 (6)	0.0169 (6)	0.0139 (5)	−0.0084 (5)	0.0024 (4)	−0.0025 (4)
S4	0.0136 (5)	0.0197 (6)	0.0151 (5)	−0.0042 (5)	0.0012 (4)	−0.0057 (4)
N3	0.0134 (19)	0.015 (2)	0.0149 (18)	−0.0048 (16)	−0.0012 (15)	−0.0004 (15)
N4	0.0065 (17)	0.0114 (18)	0.0140 (17)	0.0002 (14)	0.0005 (14)	−0.0018 (14)
C9	0.012 (2)	0.015 (2)	0.013 (2)	−0.0031 (17)	0.0027 (17)	0.0006 (17)
C10	0.015 (2)	0.017 (2)	0.014 (2)	−0.0043 (18)	0.0002 (18)	−0.0004 (17)
C11	0.007 (2)	0.015 (2)	0.012 (2)	−0.0022 (17)	−0.0010 (16)	0.0004 (16)
C12	0.0029 (19)	0.020 (2)	0.017 (2)	0.0006 (17)	0.0003 (16)	−0.0006 (18)
C13	0.011 (2)	0.013 (2)	0.017 (2)	−0.0019 (17)	−0.0004 (17)	−0.0004 (17)
C14	0.0051 (19)	0.009 (2)	0.015 (2)	−0.0003 (16)	−0.0022 (16)	0.0033 (16)
C15	0.022 (3)	0.023 (3)	0.009 (2)	−0.009 (2)	0.0028 (18)	−0.0022 (18)
C16	0.012 (2)	0.023 (3)	0.021 (2)	−0.0072 (19)	−0.0017 (19)	−0.006 (2)

Hg1—N1	2.379 (4)	Hg2—N3	2.357 (4)
Hg1—N2	2.383 (4)	Hg2—N4	2.410 (4)
Hg1—Br1	2.4970 (5)	Hg2—Br3	2.4999 (5)
Hg1—Br2	2.5206 (5)	Hg2—Br4	2.4957 (5)
S1—C2	1.709 (5)	S3—C10	1.708 (5)
S1—C1	1.727 (4)	S3—C9	1.713 (5)
S2—C5	1.708 (5)	S4—C13	1.715 (5)
S2—C4	1.729 (5)	S4—C12	1.720 (5)
N1—C1	1.309 (6)	N3—C9	1.324 (6)
N1—C3	1.389 (6)	N3—C11	1.383 (6)
N2—C4	1.298 (6)	N4—C12	1.310 (6)
N2—C6	1.388 (6)	N4—C14	1.387 (5)
C1—C7	1.480 (6)	C9—C15	1.483 (6)
C2—C3	1.368 (6)	C10—C11	1.368 (6)
C2—H2A	0.9500	C10—H10A	0.9500
C3—C6	1.467 (7)	C11—C14	1.475 (6)
C4—C8	1.496 (7)	C12—C16	1.483 (6)
C5—C6	1.358 (6)	C13—C14	1.353 (6)
C5—H5A	0.9500	C13—H13A	0.9500
C7—H7A	0.9800	C15—H15A	0.9800
C7—H7B	0.9800	C15—H15B	0.9800
C7—H7C	0.9800	C15—H15C	0.9800
C8—H8A	0.9800	C16—H16A	0.9800
C8—H8B	0.9800	C16—H16B	0.9800
C8—H8C	0.9800	C16—H16C	0.9800
N1—Hg1—N2	71.23 (13)	N3—Hg2—N4	70.25 (13)
N1—Hg1—Br1	124.79 (9)	N3—Hg2—Br4	104.07 (10)
N2—Hg1—Br1	103.63 (9)	N4—Hg2—Br4	115.64 (9)
N1—Hg1—Br2	98.36 (9)	N3—Hg2—Br3	114.30 (10)
N2—Hg1—Br2	120.67 (9)	N4—Hg2—Br3	102.77 (9)
Br1—Hg1—Br2	126.492 (16)	Br4—Hg2—Br3	132.848 (17)
C2—S1—C1	90.8 (2)	C10—S3—C9	90.6 (2)
C5—S2—C4	90.4 (2)	C13—S4—C12	90.4 (2)
C1—N1—C3	112.7 (4)	C9—N3—C11	111.5 (4)
C1—N1—Hg1	131.2 (3)	C9—N3—Hg2	130.2 (3)
C3—N1—Hg1	116.2 (3)	C11—N3—Hg2	118.3 (3)
C4—N2—C6	111.8 (4)	C12—N4—C14	112.3 (4)
C4—N2—Hg1	131.6 (3)	C12—N4—Hg2	130.9 (3)
C6—N2—Hg1	116.5 (3)	C14—N4—Hg2	116.6 (3)
N1—C1—C7	124.3 (4)	N3—C9—C15	122.7 (4)
N1—C1—S1	112.7 (3)	N3—C9—S3	113.5 (3)
C7—C1—S1	123.0 (4)	C15—C9—S3	123.8 (4)
C3—C2—S1	110.1 (3)	C11—C10—S3	110.1 (3)
C3—C2—H2A	125.0	C11—C10—H10A	125.0
S1—C2—H2A	125.0	S3—C10—H10A	125.0
C2—C3—N1	113.8 (4)	C10—C11—N3	114.4 (4)
C2—C3—C6	127.8 (4)	C10—C11—C14	128.1 (4)
N1—C3—C6	118.4 (4)	N3—C11—C14	117.5 (4)
N2—C4—C8	124.7 (4)	N4—C12—C16	123.1 (4)
N2—C4—S2	113.3 (3)	N4—C12—S4	112.9 (3)
C8—C4—S2	122.0 (4)	C16—C12—S4	124.0 (4)
C6—C5—S2	109.8 (4)	C14—C13—S4	110.1 (3)
C6—C5—H5A	125.1	C14—C13—H13A	124.9
S2—C5—H5A	125.1	S4—C13—H13A	124.9
C5—C6—N2	114.7 (4)	C13—C14—N4	114.2 (4)
C5—C6—C3	127.7 (4)	C13—C14—C11	128.8 (4)
N2—C6—C3	117.7 (4)	N4—C14—C11	117.0 (4)
C1—C7—H7A	109.5	C9—C15—H15A	109.5
C1—C7—H7B	109.5	C9—C15—H15B	109.5
H7A—C7—H7B	109.5	H15A—C15—H15B	109.5
C1—C7—H7C	109.5	C9—C15—H15C	109.5
H7A—C7—H7C	109.5	H15A—C15—H15C	109.5
H7B—C7—H7C	109.5	H15B—C15—H15C	109.5
C4—C8—H8A	109.5	C12—C16—H16A	109.5
C4—C8—H8B	109.5	C12—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
C4—C8—H8C	109.5	C12—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
N2—Hg1—N1—C1	−178.0 (4)	N4—Hg2—N3—C9	177.3 (5)
Br1—Hg1—N1—C1	88.2 (4)	Br4—Hg2—N3—C9	64.7 (4)
Br2—Hg1—N1—C1	−58.3 (4)	Br3—Hg2—N3—C9	−87.2 (4)
N2—Hg1—N1—C3	1.3 (3)	N4—Hg2—N3—C11	−4.7 (3)
Br1—Hg1—N1—C3	−92.5 (3)	Br4—Hg2—N3—C11	−117.3 (3)
Br2—Hg1—N1—C3	121.0 (3)	Br3—Hg2—N3—C11	90.8 (3)
N1—Hg1—N2—C4	−177.5 (4)	N3—Hg2—N4—C12	178.4 (4)
Br1—Hg1—N2—C4	−55.0 (4)	Br4—Hg2—N4—C12	−85.0 (4)
Br2—Hg1—N2—C4	93.8 (4)	Br3—Hg2—N4—C12	66.9 (4)
N1—Hg1—N2—C6	−0.9 (3)	N3—Hg2—N4—C14	5.4 (3)
Br1—Hg1—N2—C6	121.7 (3)	Br4—Hg2—N4—C14	101.9 (3)
Br2—Hg1—N2—C6	−89.5 (3)	Br3—Hg2—N4—C14	−106.2 (3)
C3—N1—C1—C7	179.2 (4)	C11—N3—C9—C15	176.8 (4)
Hg1—N1—C1—C7	−1.5 (7)	Hg2—N3—C9—C15	−5.0 (7)
C3—N1—C1—S1	0.6 (5)	C11—N3—C9—S3	−1.2 (5)
Hg1—N1—C1—S1	179.9 (2)	Hg2—N3—C9—S3	177.0 (2)
C2—S1—C1—N1	0.3 (4)	C10—S3—C9—N3	1.2 (4)
C2—S1—C1—C7	−178.3 (4)	C10—S3—C9—C15	−176.8 (5)
C1—S1—C2—C3	−1.2 (4)	C9—S3—C10—C11	−0.9 (4)
S1—C2—C3—N1	1.7 (5)	S3—C10—C11—N3	0.4 (5)
S1—C2—C3—C6	−177.4 (4)	S3—C10—C11—C14	178.7 (4)
C1—N1—C3—C2	−1.5 (6)	C9—N3—C11—C10	0.5 (6)
Hg1—N1—C3—C2	179.0 (3)	Hg2—N3—C11—C10	−177.9 (3)
C1—N1—C3—C6	177.7 (4)	C9—N3—C11—C14	−178.0 (4)
Hg1—N1—C3—C6	−1.7 (5)	Hg2—N3—C11—C14	3.6 (5)
C6—N2—C4—C8	−178.1 (4)	C14—N4—C12—C16	−176.9 (4)
Hg1—N2—C4—C8	−1.3 (7)	Hg2—N4—C12—C16	9.8 (7)
C6—N2—C4—S2	1.5 (5)	C14—N4—C12—S4	1.2 (5)
Hg1—N2—C4—S2	178.2 (2)	Hg2—N4—C12—S4	−172.1 (2)
C5—S2—C4—N2	−0.4 (4)	C13—S4—C12—N4	−1.5 (4)
C5—S2—C4—C8	179.2 (4)	C13—S4—C12—C16	176.6 (4)
C4—S2—C5—C6	−0.8 (4)	C12—S4—C13—C14	1.3 (4)
S2—C5—C6—N2	1.9 (5)	S4—C13—C14—N4	−0.9 (5)
S2—C5—C6—C3	−177.9 (4)	S4—C13—C14—C11	178.8 (4)
C4—N2—C6—C5	−2.2 (6)	C12—N4—C14—C13	−0.2 (6)
Hg1—N2—C6—C5	−179.5 (3)	Hg2—N4—C14—C13	174.1 (3)
C4—N2—C6—C3	177.6 (4)	C12—N4—C14—C11	−179.9 (4)
Hg1—N2—C6—C3	0.3 (5)	Hg2—N4—C14—C11	−5.6 (5)
C2—C3—C6—C5	−0.1 (8)	C10—C11—C14—C13	3.5 (8)
N1—C3—C6—C5	−179.3 (4)	N3—C11—C14—C13	−178.2 (5)
C2—C3—C6—N2	−179.9 (4)	C10—C11—C14—N4	−176.8 (5)
N1—C3—C6—N2	1.0 (6)	N3—C11—C14—N4	1.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Br4i	0.98	2.92	3.826 (5)	155
C10—H10A···Br4i	0.95	2.92	3.760 (5)	148
C16—H16B···Br3ii	0.98	2.87	3.772 (5)	154
C16—H16C···Br2iii	0.98	2.88	3.837 (5)	165

Table 1

Selected bond lengths (Å)

Hg1—N1	2.379 (4)
Hg1—N2	2.383 (4)
Hg1—Br1	2.4970 (5)
Hg1—Br2	2.5206 (5)
Hg2—N3	2.357 (4)
Hg2—N4	2.410 (4)
Hg2—Br3	2.4999 (5)
Hg2—Br4	2.4957 (5)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Br4i	0.98	2.92	3.826 (5)	155
C10—H10A⋯Br4i	0.95	2.92	3.760 (5)	148
C16—H16B⋯Br3ii	0.98	2.87	3.772 (5)	154
C16—H16C⋯Br2iii	0.98	2.88	3.837 (5)	165

Symmetry codes: (i) ; (ii) ; (iii) .