(2,2'-Dimethyl-4,4'-bi-1,3-thia-zole-κN,N')diiodidomercury(II).

In the title compound, [HgI(2)(C(8)H(8)N(2)S(2))], the Hg(II) atom is four-coordinated in a distorted tetra-hedral geometry by two N atoms from a 2,2'-dimethyl-4,4'-bithia-zole ligand and two I atoms. In the crystal structure, adjacent mol-ecules are connected by π-π contacts between the thia-zole rings [centroid-centroid distance = 3.591 (3) Å].

Related literature

For metal complexes with the 2,2′-dimethyl-4,4′-bithia­zole ligand, see: Al-Hashemi et al. (2009 ▶); Khavasi et al. (2008 ▶); Notash et al. (2008 ▶). For related structures, see: Safari et al. (2009 ▶); Tadayon Pour et al. (2008 ▶); Yousefi et al. (2008 ▶).

Experimental

Crystal data

[HgI2(C8H8N2S2)]

M = 650.67

Orthorhombic,

a = 12.9059 (10) Å

b = 14.8605 (11) Å

c = 14.9432 (11) Å

V = 2865.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 15.31 mm−1

T = 100 K

0.18 × 0.16 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.085, T max = 0.191

27850 measured reflections

3135 independent reflections

2746 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.058

S = 1.00

3135 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −1.36 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810029302/hy2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029302/hy2334Isup2.hkl

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

[HgI2(C8H8N2S2)]	Dx = 3.016 Mg m−3
Mr = 650.67	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4823 reflections
a = 12.9059 (10) Å	θ = 4–27°
b = 14.8605 (11) Å	µ = 15.31 mm−1
c = 14.9432 (11) Å	T = 100 K
V = 2865.9 (4) Å3	Prism, colorless
Z = 8	0.18 × 0.16 × 0.11 mm
F(000) = 2304

Bruker APEXII CCD diffractometer	3135 independent reflections
Radiation source: fine-focus sealed tube	2746 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 27.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.085, Tmax = 0.191	k = −18→18
27850 measured reflections	l = −19→19

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) = 0.058	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.030P)2 + 3.P] where P = (Fo2 + 2Fc2)/3
3135 reflections	(Δ/σ)max = 0.002
138 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −1.36 e Å−3

	x	y	z	Uiso*/Ueq
Hg1	0.510845 (16)	0.378820 (14)	0.225249 (14)	0.01739 (7)
I1	0.59477 (3)	0.23923 (3)	0.14062 (3)	0.02478 (10)
I2	0.46410 (3)	0.41700 (2)	0.39435 (2)	0.02213 (9)
S1	0.61688 (11)	0.68779 (9)	0.15627 (10)	0.0197 (3)
S2	0.24214 (11)	0.45250 (10)	0.00224 (9)	0.0209 (3)
N1	0.5553 (3)	0.5267 (3)	0.1740 (3)	0.0169 (9)
N2	0.3846 (3)	0.4293 (3)	0.1177 (3)	0.0158 (9)
C1	0.6287 (4)	0.5813 (4)	0.2004 (4)	0.0177 (11)
C2	0.5076 (4)	0.6562 (4)	0.1008 (4)	0.0203 (12)
H2A	0.4678	0.6948	0.0637	0.024*
C3	0.4849 (4)	0.5682 (4)	0.1169 (4)	0.0181 (11)
C4	0.3987 (4)	0.5150 (4)	0.0821 (3)	0.0166 (11)
C5	0.3287 (4)	0.5378 (4)	0.0189 (4)	0.0186 (11)
H5A	0.3278	0.5936	−0.0121	0.022*
C6	0.3056 (4)	0.3887 (4)	0.0811 (4)	0.0177 (11)
C7	0.7144 (5)	0.5550 (4)	0.2603 (4)	0.0271 (13)
H7A	0.6860	0.5350	0.3178	0.041*
H7B	0.7602	0.6066	0.2700	0.041*
H7C	0.7537	0.5057	0.2330	0.041*
C8	0.2714 (5)	0.2959 (4)	0.1047 (4)	0.0260 (13)
H8A	0.2584	0.2923	0.1692	0.039*
H8B	0.3257	0.2528	0.0882	0.039*
H8C	0.2076	0.2815	0.0721	0.039*

	U11	U22	U33	U12	U13	U23
Hg1	0.01885 (11)	0.01823 (11)	0.01509 (11)	0.00215 (8)	−0.00002 (8)	0.00063 (8)
I1	0.0298 (2)	0.0248 (2)	0.01979 (19)	0.01150 (16)	0.00339 (16)	0.00036 (15)
I2	0.0271 (2)	0.0226 (2)	0.01672 (18)	0.00144 (15)	0.00188 (14)	−0.00428 (14)
S1	0.0204 (7)	0.0173 (7)	0.0214 (7)	0.0005 (5)	−0.0012 (5)	0.0021 (5)
S2	0.0201 (7)	0.0259 (8)	0.0166 (7)	0.0026 (5)	−0.0042 (5)	0.0006 (6)
N1	0.018 (2)	0.019 (2)	0.013 (2)	0.0015 (18)	0.0012 (18)	0.0033 (18)
N2	0.016 (2)	0.018 (2)	0.013 (2)	0.0047 (17)	0.0009 (17)	−0.0022 (18)
C1	0.018 (3)	0.021 (3)	0.014 (3)	0.002 (2)	0.000 (2)	0.000 (2)
C2	0.015 (3)	0.025 (3)	0.021 (3)	0.005 (2)	0.000 (2)	−0.001 (2)
C3	0.017 (3)	0.026 (3)	0.011 (3)	0.005 (2)	0.004 (2)	0.001 (2)
C4	0.015 (3)	0.022 (3)	0.013 (3)	0.002 (2)	0.001 (2)	−0.003 (2)
C5	0.020 (3)	0.018 (3)	0.018 (3)	0.002 (2)	0.007 (2)	−0.003 (2)
C6	0.018 (3)	0.019 (3)	0.016 (3)	0.004 (2)	0.001 (2)	−0.005 (2)
C7	0.027 (3)	0.027 (3)	0.028 (3)	−0.004 (2)	−0.010 (3)	0.006 (3)
C8	0.028 (3)	0.023 (3)	0.027 (3)	−0.001 (2)	−0.007 (3)	0.000 (3)

Hg1—N1	2.397 (4)	C2—C3	1.361 (8)
Hg1—N2	2.408 (4)	C2—H2A	0.9500
Hg1—I1	2.6600 (4)	C3—C4	1.462 (8)
Hg1—I2	2.6592 (4)	C4—C5	1.349 (7)
S1—C2	1.701 (6)	C5—H5A	0.9500
S1—C1	1.721 (6)	C6—C8	1.491 (8)
S2—C5	1.708 (6)	C7—H7A	0.9800
S2—C6	1.720 (6)	C7—H7B	0.9800
N1—C1	1.309 (7)	C7—H7C	0.9800
N1—C3	1.390 (7)	C8—H8A	0.9800
N2—C6	1.304 (7)	C8—H8B	0.9800
N2—C4	1.393 (7)	C8—H8C	0.9800
C1—C7	1.475 (8)
N1—Hg1—N2	70.32 (15)	N1—C3—C4	118.4 (5)
N1—Hg1—I2	99.35 (11)	C5—C4—N2	114.2 (5)
N2—Hg1—I2	114.46 (10)	C5—C4—C3	128.5 (5)
N1—Hg1—I1	117.74 (11)	N2—C4—C3	117.3 (5)
N2—Hg1—I1	101.61 (10)	C4—C5—S2	110.7 (4)
I2—Hg1—I1	135.280 (14)	C4—C5—H5A	124.7
C2—S1—C1	90.4 (3)	S2—C5—H5A	124.7
C5—S2—C6	89.9 (3)	N2—C6—C8	124.1 (5)
C1—N1—C3	112.5 (5)	N2—C6—S2	113.9 (4)
C1—N1—Hg1	130.2 (4)	C8—C6—S2	122.1 (4)
C3—N1—Hg1	116.5 (3)	C1—C7—H7A	109.5
C6—N2—C4	111.4 (4)	C1—C7—H7B	109.5
C6—N2—Hg1	131.7 (4)	H7A—C7—H7B	109.5
C4—N2—Hg1	116.9 (3)	C1—C7—H7C	109.5
N1—C1—C7	124.1 (5)	H7A—C7—H7C	109.5
N1—C1—S1	113.0 (4)	H7B—C7—H7C	109.5
C7—C1—S1	122.9 (4)	C6—C8—H8A	109.5
C3—C2—S1	110.9 (4)	C6—C8—H8B	109.5
C3—C2—H2A	124.5	H8A—C8—H8B	109.5
S1—C2—H2A	124.5	C6—C8—H8C	109.5
C2—C3—N1	113.2 (5)	H8A—C8—H8C	109.5
C2—C3—C4	128.4 (5)	H8B—C8—H8C	109.5
N2—Hg1—N1—C1	174.2 (5)	C1—N1—C3—C2	0.1 (7)
I2—Hg1—N1—C1	61.5 (5)	Hg1—N1—C3—C2	171.1 (4)
I1—Hg1—N1—C1	−92.7 (5)	C1—N1—C3—C4	180.0 (5)
N2—Hg1—N1—C3	5.1 (3)	Hg1—N1—C3—C4	−9.0 (6)
I2—Hg1—N1—C3	−107.6 (4)	C6—N2—C4—C5	0.4 (6)
I1—Hg1—N1—C3	98.2 (4)	Hg1—N2—C4—C5	176.8 (4)
N1—Hg1—N2—C6	174.7 (5)	C6—N2—C4—C3	−179.8 (5)
I2—Hg1—N2—C6	−93.8 (5)	Hg1—N2—C4—C3	−3.5 (6)
I1—Hg1—N2—C6	59.1 (5)	C2—C3—C4—C5	8.0 (9)
N1—Hg1—N2—C4	−0.7 (3)	N1—C3—C4—C5	−171.9 (5)
I2—Hg1—N2—C4	90.8 (3)	C2—C3—C4—N2	−171.8 (5)
I1—Hg1—N2—C4	−116.3 (3)	N1—C3—C4—N2	8.4 (7)
C3—N1—C1—C7	−179.2 (5)	N2—C4—C5—S2	0.3 (6)
Hg1—N1—C1—C7	11.3 (8)	C3—C4—C5—S2	−179.5 (4)
C3—N1—C1—S1	−0.4 (6)	C6—S2—C5—C4	−0.6 (4)
Hg1—N1—C1—S1	−169.9 (2)	C4—N2—C6—C8	179.5 (5)
C2—S1—C1—N1	0.4 (4)	Hg1—N2—C6—C8	3.9 (8)
C2—S1—C1—C7	179.3 (5)	C4—N2—C6—S2	−0.9 (6)
C1—S1—C2—C3	−0.4 (4)	Hg1—N2—C6—S2	−176.6 (2)
S1—C2—C3—N1	0.2 (6)	C5—S2—C6—N2	0.9 (4)
S1—C2—C3—C4	−179.6 (4)	C5—S2—C6—C8	−179.5 (5)

Table 1

Selected bond lengths (Å)

Hg1—N1	2.397 (4)
Hg1—N2	2.408 (4)
Hg1—I1	2.6600 (4)
Hg1—I2	2.6592 (4)